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This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Synthetic route

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Reagent/catalyst; Solvent; Temperature;97%
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;97%
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h; Industry scale;
Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at 15℃; for 1h;		95%
With triethylamine; chloroacetyl chloride In dichloromethane at 0 - 20℃;83%
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

C13H16ClN3O*C18H14O8
1276666-14-8

C13H16ClN3O*C18H14O8

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: C13H16ClN3O*C18H14O8 With sodium hydroxide In dichloromethane; water at 20℃; for 1h;
Stage #2: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 10℃; for 1h;
Stage #3: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 15℃; for 1h; optical yield given as %ee;		95%
...Expand
2,5-dichloro-1,3-benzoxazole
3621-81-6

2,5-dichloro-1,3-benzoxazole

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 75℃;94%
With triethylamine In N,N-dimethyl-formamide at 75℃; for 2h;93.02%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst; Autoclave; Large scale;93.5%
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid

5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: 5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h;
Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at -10 - -5℃; for 1h;		92%
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride
1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;91%
With triethylamine; chloroacetyl chloride In dichloromethane at 0℃;88%
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In Isopropyl acetate at 20 - 25℃; Inert atmosphere;
Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With triethylamine In Isopropyl acetate; acetonitrile at 20 - 40℃; Product distribution / selectivity;
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; Isopropyl acetate In N,N-dimethyl-formamide at 20 - 25℃; for 1h; Inert atmosphere;
Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With Isopropyl acetate; potassium carbonate In water; N,N-dimethyl-formamide at 0 - 5℃; for 1.25h; Concentration; Solvent; Reagent/catalyst;		14.4 g
5-chloro-2-mercaptobenzoxazole
22876-19-3

5-chloro-2-mercaptobenzoxazole

(R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride

(R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: 5-chloro-2-mercaptobenzoxazole With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.916667h;
Stage #2: (R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride With triethylamine In N,N-dimethyl-formamide at 20 - 37℃; for 0.5h;		76%
5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

A

Suvorexant
1030377-33-3

Suvorexant

B

C23H23ClN6O2

C23H23ClN6O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 5 - 10℃; for 1.5h;A 68%
B n/a
...Expand
1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

5-chloro-benzoxazole
17200-29-2

5-chloro-benzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With acetic acid In acetonitrile at 20℃; for 8h; Electrolysis;64.66%
With oxygen; copper diacetate; acetic acid In acetonitrile at 70℃; for 4h;3.3 g
2-iodoyl-5-methylbenzoic acid
52548-14-8

2-iodoyl-5-methylbenzoic acid

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 40 °C
1.2: 20 °C
2.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C
2.2: 1 h / 0 - 10 °C
2.3: 1 h / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / tetrahydrofuran; water / 3 h / 22 - 25 °C / Inert atmosphere
1.2: 19 h / 21 - 23 °C / Inert atmosphere
2.1: oxalyl dichloride / Isopropyl acetate; N,N-dimethyl-formamide / 3 h / 20 - 25 °C / Inert atmosphere
3.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / copper(l) iodide / N,N-dimethyl-formamide; tetrahydrofuran / 40 - 65 °C / Industry scale
1.2: 20 °C
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
2.2: 1 h / 15 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide
2: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
4: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
2-bromo-5-chlorobenzo[d]oxazole
1251033-26-7

2-bromo-5-chlorobenzo[d]oxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetonitrile / Inert atmosphere
2: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: acetonitrile / Inert atmosphere
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol
1356342-15-8

2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
1.2: 1.25 h / 0 - 10 °C
2.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
3.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
3.2: 1.25 h / 0 - 5 °C
View Scheme
C13H15ClN2O3
1383717-09-6

C13H15ClN2O3

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
2: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
3: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester
1383717-11-0

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
2: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
2.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
2.2: 1.25 h / 0 - 5 °C
View Scheme
5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride
1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With potassium carbonate In Isopropyl acetate; water at 0℃; for 1.25h; Inert atmosphere;14.4 g
2-hydroxy-5-chloro-aniline
95-85-2

2-hydroxy-5-chloro-aniline

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 0 - 5 °C / Industry scale
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale
2.2: 2.5 h / 10 - 20 °C
2.3: 10 h / 20 °C
3.1: hydrogenchloride; water / 10 h / 20 - 30 °C
3.2: 35 °C / pH > 10
3.3: 24 h / -5 °C / Inert atmosphere
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
4.2: 1 h / 15 °C
View Scheme
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Reagent/catalyst; Solvent; Temperature;97%
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;97%
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h; Industry scale;
Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at 15℃; for 1h;		95%
With triethylamine; chloroacetyl chloride In dichloromethane at 0 - 20℃;83%
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

C13H16ClN3O*C18H14O8
1276666-14-8

C13H16ClN3O*C18H14O8

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: C13H16ClN3O*C18H14O8 With sodium hydroxide In dichloromethane; water at 20℃; for 1h;
Stage #2: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 10℃; for 1h;
Stage #3: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 15℃; for 1h; optical yield given as %ee;		95%
...Expand
2,5-dichloro-1,3-benzoxazole
3621-81-6

2,5-dichloro-1,3-benzoxazole

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 75℃;94%
With triethylamine In N,N-dimethyl-formamide at 75℃; for 2h;93.02%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Reagent/catalyst; Autoclave; Large scale;93.5%
5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid

5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: 5-methyl-2-(1H-1,2,3-triazol-2-yl)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 10℃; for 1h;
Stage #2: 5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole With triethylamine In dichloromethane at -10 - -5℃; for 1h;		92%
2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid
956317-36-5

2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride
1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;91%
With triethylamine; chloroacetyl chloride In dichloromethane at 0℃;88%
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In Isopropyl acetate at 20 - 25℃; Inert atmosphere;
Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With triethylamine In Isopropyl acetate; acetonitrile at 20 - 40℃; Product distribution / selectivity;
Stage #1: 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid With oxalyl dichloride; Isopropyl acetate In N,N-dimethyl-formamide at 20 - 25℃; for 1h; Inert atmosphere;
Stage #2: 5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride With Isopropyl acetate; potassium carbonate In water; N,N-dimethyl-formamide at 0 - 5℃; for 1.25h; Concentration; Solvent; Reagent/catalyst;		14.4 g
5-chloro-2-mercaptobenzoxazole
22876-19-3

5-chloro-2-mercaptobenzoxazole

(R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride

(R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Stage #1: 5-chloro-2-mercaptobenzoxazole With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.916667h;
Stage #2: (R)-(7-methyl-1,4-diazepan-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride With triethylamine In N,N-dimethyl-formamide at 20 - 37℃; for 0.5h;		76%
5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole
1266975-27-2

5-chloro-2-[(5R)-hexahydro-5-methyl-1H-1,4-diazepin-1-yl]benzoxazole

A

Suvorexant
1030377-33-3

Suvorexant

B

C23H23ClN6O2

C23H23ClN6O2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 5 - 10℃; for 1.5h;A 68%
B n/a
...Expand
1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

5-chloro-benzoxazole
17200-29-2

5-chloro-benzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With acetic acid In acetonitrile at 20℃; for 8h; Electrolysis;64.66%
With oxygen; copper diacetate; acetic acid In acetonitrile at 70℃; for 4h;3.3 g
2-iodoyl-5-methylbenzoic acid
52548-14-8

2-iodoyl-5-methylbenzoic acid

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: copper(l) iodide; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 40 °C
1.2: 20 °C
2.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C
2.2: 1 h / 0 - 10 °C
2.3: 1 h / 0 - 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / tetrahydrofuran; water / 3 h / 22 - 25 °C / Inert atmosphere
1.2: 19 h / 21 - 23 °C / Inert atmosphere
2.1: oxalyl dichloride / Isopropyl acetate; N,N-dimethyl-formamide / 3 h / 20 - 25 °C / Inert atmosphere
3.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / copper(l) iodide / N,N-dimethyl-formamide; tetrahydrofuran / 40 - 65 °C / Industry scale
1.2: 20 °C
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
2.2: 1 h / 15 °C
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide
2: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
4: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
2-bromo-5-chlorobenzo[d]oxazole
1251033-26-7

2-bromo-5-chlorobenzo[d]oxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetonitrile / Inert atmosphere
2: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: acetonitrile / Inert atmosphere
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
3: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
4: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
5: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol
1356342-15-8

2-[(5-chloro-1,3-benzoxazol-2-yl)amino]ethanol

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
2: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
3: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
4: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
1.2: 1.25 h / 0 - 10 °C
2.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
3.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
3.2: 1.25 h / 0 - 5 °C
View Scheme
C13H15ClN2O3
1383717-09-6

C13H15ClN2O3

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
2: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
3: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester
1383717-11-0

methanesulfonic acid 2-[(5-chloro-benzooxazol-2-yl)-(3-oxo-butyl)amino]ethyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
2: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
2.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
2.2: 1.25 h / 0 - 5 °C
View Scheme
5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride
1104546-96-4

5-methyl-2-(2Η-1,2,3-triazol-2-yl)benzoyl chloride

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride
1266664-66-7

5-chloro-2-((R)-5-methyl-[1,4]diazepan-1-yl)benzooxazole hydrochloride

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With potassium carbonate In Isopropyl acetate; water at 0℃; for 1.25h; Inert atmosphere;14.4 g
2-hydroxy-5-chloro-aniline
95-85-2

2-hydroxy-5-chloro-aniline

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / tetrahydrofuran / 60 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
2.2: 3.33 h / -20 - -15 °C / Inert atmosphere
3.1: acetonitrile / Inert atmosphere
4.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
5.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
6.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
7.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: water; methanol / 0 - 5 °C / Industry scale
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale
2.2: 2.5 h / 10 - 20 °C
2.3: 10 h / 20 °C
3.1: hydrogenchloride; water / 10 h / 20 - 30 °C
3.2: 35 °C / pH > 10
3.3: 24 h / -5 °C / Inert atmosphere
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
4.2: 1 h / 15 °C
View Scheme
5-chloro-benzoxazole
17200-29-2

5-chloro-benzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
1.2: 3.33 h / -20 - -15 °C / Inert atmosphere
2.1: acetonitrile / Inert atmosphere
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 23 °C / Inert atmosphere
4.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
5.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
6.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.83 h / -25 - -15 °C / Inert atmosphere
1.2: 3.33 h / -20 - -15 °C / Inert atmosphere
2.1: acetonitrile / Inert atmosphere
3.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
4.1: triethylamine / Isopropyl acetate / 1.25 h / 0 - 10 °C / Inert atmosphere
5.1: sitagliptin transaminase CDX-017; triethanolamine; pyridoxal 5'-phosphate; isopropylamine hydrochloride / water; dimethyl sulfoxide / 11 h / 40 °C / pH 9.5 / Inert atmosphere
6.1: potassium carbonate / Isopropyl acetate; water / 1.25 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 4.73 h / -52 - 12.5 °C / Inert atmosphere
1.2: 3.33 h / -25 - 20 °C
1.3: 20 - 27 °C
2.1: sodium hydroxide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
2.2: 1.25 h / 0 - 10 °C
3.1: isopropylamine hydrochloride; triethanolamine; pyridoxal 5'-phosphate; isopropylamine mesylate / water; dimethyl sulfoxide / 11 h / 40 °C / pH 8.5 / Enzymatic reaction
4.1: oxalyl dichloride; Isopropyl acetate / N,N-dimethyl-formamide / 1 h / 20 - 25 °C / Inert atmosphere
4.2: 1.25 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: acetic acid / acetonitrile / 6 h / 20 °C / Electrolysis
2: hydrogenchloride / 1,4-dioxane; water / 3 h / 20 °C
3: 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h / 20 °C
View Scheme
5-chloro-2-mercaptobenzoxazole
22876-19-3

5-chloro-2-mercaptobenzoxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale
1.2: 2.5 h / 10 - 20 °C
1.3: 10 h / 20 °C
2.1: hydrogenchloride; water / 10 h / 20 - 30 °C
2.2: 35 °C / pH > 10
2.3: 24 h / -5 °C / Inert atmosphere
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
3.2: 1 h / 15 °C
View Scheme
Multi-step reaction with 4 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1.75 h / 25 °C / Industry scale
1.2: 2.5 h / 10 - 20 °C
1.3: 10 h / 20 °C
2.1: tetrahydrofuran / 25 - 60 °C / Industry scale
3.1: potassium carbonate / dichloromethane; water / -5 - 20 °C / Industry scale; Inert atmosphere
3.2: 16.5 h / -10 - -5 °C
3.3: 0 °C / pH > 11
4.1: oxalyl dichloride / N,N-dimethyl-formamide / Isopropyl acetate / 20 - 25 °C / Inert atmosphere
4.2: 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.83 h / 20 °C
2: triethylamine / N,N-dimethyl-formamide / 39 h / 20 - 90 °C
View Scheme
4-[(2-amino-ethyl)-(5-chlorobenzoxazol-2-yl)amino]butan-2-one-bis-methanesulfonic acid salt

4-[(2-amino-ethyl)-(5-chlorobenzoxazol-2-yl)amino]butan-2-one-bis-methanesulfonic acid salt

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / dichloromethane; water / -5 - 20 °C / Industry scale; Inert atmosphere
1.2: 16.5 h / -10 - -5 °C
1.3: 0 °C / pH > 11
2.1: oxalyl dichloride / N,N-dimethyl-formamide / Isopropyl acetate / 20 - 25 °C / Inert atmosphere
2.2: 20 - 40 °C
View Scheme
{2-[(5-chlorobenzooxazol-2-yl)-(3-oxobutyl)amino]ethyl}carbamic acid tert-butyl ester
1276666-10-4

{2-[(5-chlorobenzooxazol-2-yl)-(3-oxobutyl)amino]ethyl}carbamic acid tert-butyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; water / 10 h / 20 - 30 °C
1.2: 35 °C / pH > 10
1.3: 24 h / -5 °C / Inert atmosphere
2.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 1 h / 0 - 10 °C / Industry scale
2.2: 1 h / 15 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 25 - 60 °C / Industry scale
2.1: potassium carbonate / dichloromethane; water / -5 - 20 °C / Industry scale; Inert atmosphere
2.2: 16.5 h / -10 - -5 °C
2.3: 0 °C / pH > 11
3.1: oxalyl dichloride / N,N-dimethyl-formamide / Isopropyl acetate / 20 - 25 °C / Inert atmosphere
3.2: 20 - 40 °C
View Scheme
C21H30N2O

C21H30N2O

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium hydroxide / 1,4-dioxane; water / 2.5 h / 0 - 20 °C
2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 20 h / 760.05 Torr
3: sodium hydrogencarbonate / tetrahydrofuran; water / 23 h / 0 °C
4: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / toluene / 17 h / 20 °C
5: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
7: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
8: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
C11H24N2O3

C11H24N2O3

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydrogencarbonate / tetrahydrofuran; water / 23 h / 0 °C
2: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / toluene / 17 h / 20 °C
3: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
6: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone
1030377-32-2

1-(7(R)-methyl-1,4-diazepan-1-yl)-1-[5-methyl-2-(2H-1,2,3-triazole-2-yl)phenyl]methanone

2-bromo-5-chlorobenzo[d]oxazole
1251033-26-7

2-bromo-5-chlorobenzo[d]oxazole

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20 - 65℃; for 5h;
(3R)-3-[benzyl((1R)-1-phenylethyl)amino]-N-(2-hydroxyethyl)butyramide

(3R)-3-[benzyl((1R)-1-phenylethyl)amino]-N-(2-hydroxyethyl)butyramide

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
2: sodium hydroxide / 1,4-dioxane; water / 2.5 h / 0 - 20 °C
3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 20 h / 760.05 Torr
4: sodium hydrogencarbonate / tetrahydrofuran; water / 23 h / 0 °C
5: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / toluene / 17 h / 20 °C
6: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
7: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
8: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
9: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
(3R)-{3-[benzyl((1R)-1-phenylethyl)amino]butyl}(2-hydroxyethyl)carbamic acid tert-butyl ester

(3R)-{3-[benzyl((1R)-1-phenylethyl)amino]butyl}(2-hydroxyethyl)carbamic acid tert-butyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 20 h / 760.05 Torr
2: sodium hydrogencarbonate / tetrahydrofuran; water / 23 h / 0 °C
3: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / toluene / 17 h / 20 °C
4: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
6: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
7: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
(2-hydroxyethyl)[(R)-3-(2-nitrobenzenesulfonylamino)butyl]carbamic acid tert-butyl ester

(2-hydroxyethyl)[(R)-3-(2-nitrobenzenesulfonylamino)butyl]carbamic acid tert-butyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triphenylphosphine; azodicarboxylic acid bis(2-methoxyethyl) ester / toluene / 17 h / 20 °C
2: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
5: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
(R)-5-methyl-4-(2-nitrobenzenesulfonyl)[1,4]diazepane-1-carboxylic acid tert-butyl ester

(R)-5-methyl-4-(2-nitrobenzenesulfonyl)[1,4]diazepane-1-carboxylic acid tert-butyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; thiophenol / acetonitrile / 17 h / 60 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
4: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
(5R)-5-methyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester

(5R)-5-methyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3: potassium carbonate / acetonitrile / 5 h / 20 - 65 °C
View Scheme
(R)-methyl-2-(N-benzyl-3-((tert-butoxycarbonyl)amino)butyramido)acetate

(R)-methyl-2-(N-benzyl-3-((tert-butoxycarbonyl)amino)butyramido)acetate

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrogenchloride / ethyl acetate / 4 h
2: sodium methylate / methanol / 20 °C / Inert atmosphere
3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
4: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
5: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
6: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / ethyl acetate / 4 h / 25 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 25 °C / Cooling with ice
3: benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 2 h / 50 °C
4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 25 °C
5: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
(R)-4-benzyl-7-methyl-1,4-diazepane-2,5-dione

(R)-4-benzyl-7-methyl-1,4-diazepane-2,5-dione

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
4: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 25 °C / Cooling with ice
2: benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 2 h / 50 °C
3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 25 °C
4: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
(R)-1-benzyl-5-methyl-1,4-diazepane

(R)-1-benzyl-5-methyl-1,4-diazepane

Suvorexant
1030377-33-3

Suvorexant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C
2: palladium 10% on activated carbon; hydrogen / methanol / 4 h / 20 °C
3: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 2 h / 50 °C
2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 25 °C
3: triethylamine / N,N-dimethyl-formamide / 2 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: / dichloromethane / 18 - 25 °C / Large scale
2: LACTIC ACID / methanol / 30 - 35 °C / Inert atmosphere; Large scale
3: triethylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Autoclave; Large scale
View Scheme
Suvorexant
1030377-33-3

Suvorexant

C23H20(2)H3ClN6O2

C23H20(2)H3ClN6O2

Conditions
ConditionsYield
With deuterium In tetrahydrofuran under 1500.15 Torr; for 24h; Glovebox; Heating;99%

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