Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 24785804, compound

HRID 2239344Notes

Reaction equation

HRID 2239344 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])C)=[O:4].[CH3:22][N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][O:30][C:31]2[CH:32]=[C:33](CN)[CH:34]=[CH:35][CH:36]=2)[CH2:25][CH2:24]1>CO>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2[S:6][C:5]3[C:3](=[O:4])[N:12]([CH2:14][C:35]4[CH:34]=[CH:33][CH:32]=[C:31]([O:30][CH2:29][CH:26]5[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]5)[CH:36]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 68710204HCID 68710204, compound

Product 1

HCID 24785804HCID 24785804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.165 g, 0.51 mmol) and 1-{3-[(1-methylpiperidin-4-yl)methoxy]phenyl}-methanamine (0.100 g, 0.43 mmol) in MeOH (2 mL) was heated by microwave at 120° C. in 20 minutes, cooled, the formed precipitate filtered off and washed with MeOH to give the title compound as a white solid. Yield: 0.075 g (31%). 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.58-7.63 (m, 2H), 7.45 (s, 1H), 7.38-7.43 (m, 2H), 7.22 (m, 1H), 6.79-6.91 (m, 3H), 5.17 (s, 2H), 3.76 (d, 2H, J=6.4 Hz), 2.82-2.89 (m, 2H), 2.25 (s, 3H), 1.87-1.96 (m, 2H), 1.76-1.83 (m, 2H), 1.68-1.76 (m, 1H), 1.32-1.44 (m, 2H).

Workup

  1. temperaturecooled
  2. filtrationthe formed precipitate filtered off
  3. washwashed with MeOH

Sources & evidence

ORD record
ord-eb7727ad9a6342be9fe80ed1d47876ea
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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