1
1.1 rt
→
140°C; 2 h, 135-140°C; 140°C
→
80°C
Reactants: 2, Stages: 1
References
An improved process for the preparation of
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, a key intermediate in the synthesis of glimepiride
By Dhansukhlal, Vyas Ketan et al
From Indian Pat. Appl., 2006MU00502, 26 Jun 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproduced under license. All Rights Reserved.
Reaction
Stages
Notes
Yield
2
1.1 R:ClSO3H, S:CH2Cl2, -2 - 0°C; 6 h, -5 - 0°C
1.2 R:H2O, cooled
Reactants: 1, Reagents: 2,
Solvents: 1, Stages: 2
References
An improved process for the preparation of
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, a key intermediate in the synthesis of glimepiride
By Dhansukhlal, Vyas Ketan et al
From Indian Pat. Appl., 2006MU00502, 26 Jun 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproduced under license. All Rights Reserved.
Reaction
Stages
Notes
Yield
3
1.1 R:NH3, S:AcOEt, 30-45°C; 45°C
→
75°C; 6 h,
70-75°C; 75°C
→
30°C
Reactants: 1, Reagents: 1,
Solvents: 1, Stages: 1
References
An improved process for the preparation of
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, a key intermediate in the synthesis of glimepiride
By Dhansukhlal, Vyas Ketan et al
From Indian Pat. Appl., 2006MU00502, 26 Jun 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproduced under license. All Rights Reserved.
Reaction
Stages
Notes
Yield
4
1.1 R:Et3N, R:ClCO2Et, S:CH2Cl2, 2 h, 20-25°C
1.2 R:AcOH, S:H2O, pH 4-4.2; 30 min
1.3 R:4-DMAP, S:PhMe, rt
→
reflux; 3 h, reflux; reflux
→
30°C; 3 h, 25-30°C
alternative preparation shown,
Reactants: 2, Reagents: 4,
Solvents: 3, Stages: 3
References
An improved process for the preparation of
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, a key intermediate in the synthesis of glimepiride
By Dhansukhlal, Vyas Ketan et al
From Indian Pat. Appl., 2006MU00502, 26 Jun 2009
CASREACT ®: Copyright © 2011 American Chemical Society. All Rights Reserved. CASREACT contains reactions from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006 John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Synthesis Inc. Reproduced under license. All Rights Reserved.
C16 H21 N3 O4 S 1H-Pyrrole-1-carboxamide, N-[2-[4- (aminosulfonyl)phenyl]ethyl]-3-ethyl-2,5-dihydro- 4-methyl-2-oxo-~25 References Reactions Commercial Sources Regulatory Information C16 H19 Cl N2 O4 S
Benzenesulfonyl chloride, 4-[2-[[(3-ethyl-2,5- dihydro-4-methyl-2-oxo-1H-pyrrol-1- yl)carbonyl]amino]ethyl]-~6 References Reactions Commercial Sources Regulatory Information C9 H9 N O Benzene, (2-isocyanatoethyl)-~455 References Reactions Commercial Sources Regulatory Information 247098-18-6 C16 H20 N2 O2 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro- 4-methyl-2-oxo-N-(2-phenylethyl)-~9 References Reactions Commercial Sources Regulatory Information 32175-00-1 Relative stereochemistry. C8 H13 N O
Cyclohexane, 1-isocyanato-4-methyl-,
trans-~29 References Reactions Commercial Sources Regulatory Information 766-36-9 C7 H11 N O 2H-Pyrrol-2-one, 3-ethyl-1,5-dihydro-4-methyl-~36 References Reactions Commercial Sources Regulatory Information 93479-97-1 Relative stereochemistry. C24 H34 N4 O5 S 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro- 4-methyl-N-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl ]phenyl]ethyl]-2-oxo-~1491 References Reactions Commercial Sources Regulatory Information