• Name

  Iguratimod

• EINECS 808-127-0
• CAS No. 123663-49-0
• Article Data5
• CAS DataBase
• Density 1.52 g/cm³
• Solubility
• Melting Point 238.0 to 242.0 °C
• Formula C₁₇H₁₄N₂O₆S
• Boiling Point 580.6 °C at 760 mmHg
• Molecular Weight 374.374
• Flash Point 304.9 °C
• Transport Information
• Appearance white powder
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms T 614;T614 (antiinflammatory);Ailamode;3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one;N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide;
• PSA 123.09000
• LogP 4.38780

Synthetic route

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

149457-03-4

α-formamido-2'-hydroxy-4'-methanesulfonamido-5'-phenoxyacetophenone

123663-49-0

Iguratimod

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 15℃; for 8h; Cyclization;	87%

2258-42-6

Acetic formic anhydride

123663-48-9

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide

123663-49-0

Iguratimod

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h; Formylation;	73%

123663-48-9

N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide

123663-49-0

Iguratimod

Conditions

Conditions	Yield
With formic acid; acetic anhydride In dichloromethane; di-isopropyl ether	73%

84594-95-6

4-methoxy-2-nitro-1-phenoxybenzene

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 4: 91 percent / acetone / 3 h 5: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 6: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme
Multi-step reaction with 9 steps 1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 4: 70 percent aq. HClO4 / 1 h / 20 °C 5: H2O / 0.08 h / Heating 6: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 7: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 8: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 9: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

76838-72-7

5-methoxy-2-phenoxyaniline

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / pyridine / 1 h / 20 °C 2: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 3: 91 percent / acetone / 3 h 4: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 5: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme
Multi-step reaction with 8 steps 1: 82 percent / pyridine / 1 h / 20 °C 2: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 3: 70 percent aq. HClO4 / 1 h / 20 °C 4: H2O / 0.08 h / Heating 5: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 6: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 7: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 8: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

10298-80-3

2-chloro-5-methoxynitrobenzene

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 5: 91 percent / acetone / 3 h 6: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 7: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme
Multi-step reaction with 10 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 5: 70 percent aq. HClO4 / 1 h / 20 °C 6: H2O / 0.08 h / Heating 7: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 8: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 9: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 10: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

123664-84-6

N-(5-methoxy-2-phenoxyphenyl)methanesulfonamide

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 2: 91 percent / acetone / 3 h 3: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 4: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme
Multi-step reaction with 7 steps 1: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 2: 70 percent aq. HClO4 / 1 h / 20 °C 3: H2O / 0.08 h / Heating 4: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 5: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 6: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 7: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

123664-52-8

methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 70 percent aq. HClO4 / 1 h / 20 °C 2: H2O / 0.08 h / Heating 3: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 4: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 5: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 6: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

123662-55-5

7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 2: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 3: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 4: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

123664-21-1

N-(4-oxo-6-phenoxy-2,3-dihydro-4H-7-chromenyl)methanesulfonamide

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 2: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 3: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

123664-34-6

3-bromo-2,3-dihydro-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 2: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

149456-98-4

N-(2-(2-methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 2: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme

α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / acetone / 3 h 2: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 3: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme

4-ethoxy-7-methanesulfonylamino-6-phenoxy-chromenylium; perchlorate

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: H2O / 0.08 h / Heating 2: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 3: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 4: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 5: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

108-95-2

phenol

pentacarbonyl(3-cyclohex-1-enyl-1-ethoxy-2-propyn-1-ylidene)tungsten

pentacarbonyl(3-cyclohex-1-enyl-1-ethoxy-2-propyn-1-ylidene)tungsten

123663-49-0

Iguratimod

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 5: 91 percent / acetone / 3 h 6: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 7: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme
Multi-step reaction with 10 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 5: 70 percent aq. HClO4 / 1 h / 20 °C 6: H2O / 0.08 h / Heating 7: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 8: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 9: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 10: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme

761454-93-7

N-[3-(formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide monohydrate

123663-49-0

Iguratimod

Conditions

Conditions	Yield
at 160℃; for 1h; Product distribution / selectivity;
In acetonitrile at 25℃; for 24h; Product distribution / selectivity;

123663-49-0

Iguratimod

74-88-4

methyl iodide

3-(N-formyl-N-methyl)amino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

Conditions

Conditions	Yield
In diethyl ether; water; N,N-dimethyl-formamide	75%

123663-49-0

Iguratimod

761454-93-7

N-[3-(formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide monohydrate

Conditions

Conditions	Yield
With water at 25℃; for 168h; Product distribution / selectivity;
With water at 25℃; for 24h; Product distribution / selectivity;

Iguratimod Chemical Properties