1,2-Dichloroethane → N-[4-(dimethylaminoimino)phenyl]-5N-(4-chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxamide

HRID 1432553Notes

Reaction equation

HRID 1432553 reaction equation
ClC1C=CC(NC([C:11]2[S:19][C:18]3[CH2:17][CH:16]([C:20]([OH:22])=O)[NH:15][CH2:14][C:13]=3[CH:12]=2)=O)=CC=1.[CH3:23][N:24]([N:26]=[C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH2:28]1)[CH3:25].[CH2:34]([Cl:37])[CH2:35]Cl.[OH2:38]>CN(C=O)C>[CH3:25][N:24]([N:26]=[C:27]1[CH:28]=[CH:29][C:30]([NH:33][C:20]([CH:16]2[N:15]([C:14]([NH:15][C:16]3[CH:20]=[CH:35][C:34]([Cl:37])=[CH:18][CH:17]=3)=[O:38])[CH2:14][C:13]3[CH:12]=[CH:11][S:19][C:18]=3[CH2:17]2)=[O:22])=[CH:31][CH2:32]1)[CH3:23]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 686968834-(Dimethylaminoimino)phenylamineHCID 131727718(4-Chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid

Product 1

HCID 86606524N-[4-(dimethylaminoimino)phenyl]-5N-(4-chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5N-(4-chlorophenylaminocarbonyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid (42 mg, 0.12 mmol) and 4-(dimethylaminoimino)phenylamine (42 mg, 0.26 mmol) in DMF (3 mL) and H2O (0.5 mL) at room temperature, EDC (72 mg, 0.38 mmol) was added. The mixture was stirred at room temperature overnight. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (26 mg). MS 482.3 and 484.4 (M+H, Cl pattern).

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-7e53d070e0c447f498207f7edd452464
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

Loading…