Product Name

  • Name

    Ramatroban

  • EINECS
  • CAS No. 116649-85-5
  • Article Data2
  • CAS DataBase
  • Density 1.43 g/cm3
  • Solubility
  • Melting Point 134-135°
  • Formula C21H21FN2O4S
  • Boiling Point 654.7 °C at 760 mmHg
  • Molecular Weight 416.473
  • Flash Point 349.7 °C
  • Transport Information
  • Appearance Crystalline solid.
  • Safety 26-36/37/39-45
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 116649-85-5 (Ramatroban)
  • Hazard Symbols Xi
  • Synonyms 9H-Carbazole-9-propanoicacid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (R)-;BAY-u3405;Baynas;9H-Carbazole-9-propanoicacid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)-;
  • PSA 96.78000
  • LogP 4.56260

Synthetic route

(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide
118699-38-0

(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Stage #1: (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide With water; sodium hydroxide In isopropyl alcohol at 100℃; for 24h;
Stage #2: With hydrogenchloride In water		79%
acrylonitrile
107-13-1

acrylonitrile

(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
116650-36-3

(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
With potassium hydroxide; sodium hydride 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h; Yield given. Multistep reaction;
1,2,3,4-tetrahydrocarbazol-3-one
51145-61-0

1,2,3,4-tetrahydrocarbazol-3-one

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2.) tetrabutylammonium borohydride, 3.) 2N sulfuric acid / 1.) benzene, reflux, 1 h, 2.) CH2Cl2, -50 deg C to room temperature, 3.) methanol, room temperature, 1 h
2: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min
3: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
4: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
Multi-step reaction with 6 steps
1.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 10 h / -25 - -15 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
2.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
3.2: 10 h / -25 - -15 °C
4.1: water; triphenylphosphine / 15 h / 65 °C
5.1: triethylamine / dichloromethane / 1 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
6.2: 1 h / 20 °C
7.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(3R)-3-(1S-phenylethylamino)-1,2,3,4-tetrahydrocarbazole hydrogensulfate

(3R)-3-(1S-phenylethylamino)-1,2,3,4-tetrahydrocarbazole hydrogensulfate

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min
2: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
3: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
(3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine
116650-33-0

(3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
2: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
2.2: 1 h / 20 °C
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(S)-2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate
1374648-17-5

(S)-2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(R)-3-azido-2,3,4,9-tetrahydro-1H-carbazole
1374648-18-6

(R)-3-azido-2,3,4,9-tetrahydro-1H-carbazole

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; triphenylphosphine / 15 h / 65 °C
2.1: triethylamine / dichloromethane / 1 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
3.2: 1 h / 20 °C
4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
116650-12-5

4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
1.2: 20 °C
2.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
2.2: 1 h / 20 °C
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
2: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate

2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium azide / 24 h
2.1: chiralcel OD / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium azide / 24 h
2.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
3.1: triethylamine / dichloromethane / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
4.2: 20 °C
5.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: sodium azide / 24 h
2.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
3.1: triethylamine / dichloromethane / 20 °C
4.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: chiralcel OD / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
2.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: chiralcel OD / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
2.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(S)-(-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
1374648-14-2

(S)-(-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
1.2: 10 h / -25 - -15 °C
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
128432-38-2, 14384-34-0

(+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 10 h / -25 - -15 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 10 h / -25 - -15 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 6 steps
1.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 10 h / -25 - -15 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
2.2: 1 h / 20 °C
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
3-azido-2,3,4,9-tetrahydro-1H-carbazole

3-azido-2,3,4,9-tetrahydro-1H-carbazole

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
2.1: triethylamine / dichloromethane / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
3.2: 20 °C
4.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
2.1: triethylamine / dichloromethane / 20 °C
3.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: chiralcel OD / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine
61894-99-3, 116650-33-0, 116650-34-1, 134525-54-5

2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
2.2: 20 °C
3.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / 20 °C
2.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
3.2: 1 h / 20 °C
4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
phenylhydrazine
100-63-0

phenylhydrazine

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide
116650-36-3

(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
1.2: 1 h / 20 °C
2.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane]
54621-12-4

1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane]

ramatroban
116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: trifluoroacetic acid / acetone / 24 h / 65 °C
2.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
3.2: 10 h / -25 - -15 °C
4.1: water; triphenylphosphine / 15 h / 65 °C
5.1: triethylamine / dichloromethane / 1 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
6.2: 1 h / 20 °C
7.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 8 steps
1.1: trifluoroacetic acid / acetone / 24 h / 65 °C
2.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction
3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
5.1: water; triphenylphosphine / 15 h / 65 °C
6.1: triethylamine / dichloromethane / 1 h / 20 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
7.2: 1 h / 20 °C
8.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 8 steps
1.1: trifluoroacetic acid / acetone / 24 h / 65 °C
2.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
4.2: 10 h / -25 - -15 °C
5.1: water; triphenylphosphine / 15 h / 65 °C
6.1: triethylamine / dichloromethane / 1 h / 20 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
7.2: 1 h / 20 °C
8.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
methanol
67-56-1

methanol

ramatroban
116649-85-5

ramatroban

(R)-methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate
141307-19-9

(R)-methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate

Conditions
ConditionsYield
With sulfuric acid In water at 65℃; for 15h;60%
ramatroban
116649-85-5

ramatroban

(3R)-3-(4-fluorophenylsulfonamido)-1,2,3,4-terahydro-9-carbazolepropanoic acid sodium salt

(3R)-3-(4-fluorophenylsulfonamido)-1,2,3,4-terahydro-9-carbazolepropanoic acid sodium salt

Conditions
ConditionsYield
With sodium hydroxide

Ramatroban Specification

1. Introduction of Ramatroban
Ramatroban is an approved human medication for the treatment of allergic rhinitis that has documented activity as an antagonist. The IUPAC Name of it is 3-[(3R)-3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoic acid. What's more, Ramatroban is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.

2. Properties of Ramatroban
Boiling point: 654.7 °C at 760 mmHg
Flash Point: 349.7 °C
Density: 1.43 g/cm3
Surface Tension: 56 dyne/cm
Enthalpy of Vaporization: 101.32 kJ/mol
Vapour Pressure: 4.94E-18 mmHg at 25°C
XLogP3-AA: 2.9
H-Bond Donor: 2
H-Bond Acceptor: 6

3. Structure Descriptors of Ramatroban
Canonical SMILES: C1CC2=C(CC1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
Isomeric SMILES: C1CC2=C(C[C@@H]1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
InChI: InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1  
InChIKey: LDXDSHIEDAPSSA-OAHLLOKOSA-N

4. Use of Ramatroban
Ramatroban is used for the treatment of allergic rhinitis as an antagonist of the thromboxane receptor. It is also an antagonist of the DP2 receptor with IC50 values of 100-170 nM. It is more potent at the DP2 receptor than the TP receptor by 4-5 fold. It is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.

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