Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 24782492, compound

HRID 2239358Notes

Reaction equation

HRID 2239358 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][CH2:26][C:25]([CH2:30][O:31][C:32]2[CH:33]=[C:34](CN)[CH:35]=[CH:36][CH:37]=2)([CH3:29])[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:36]4[CH:35]=[CH:34][CH:33]=[C:32]([O:31][CH2:30][C:25]5([CH3:29])[CH2:26][CH2:27][CH2:28][N:23]([CH3:22])[CH2:24]5)[CH:37]=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 68709013HCID 68709013, compound

Product 1

HCID 24782492HCID 24782492, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.16 g, 0.5 mmol), 1-{3-[(1,3-dimethylpiperidin-3-yl)methoxy]phenyl}methanamine (0.10 g, 0.4 mmol) in MeOH (2 mL) were heated by microwave at 120° C. for 20 minutes. The reaction mixture was allowed to cool to room temperature and the precipitate was filtered off and washed with MeOH to give the title compound as a solid. Yield: 0.12 g (49%). 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.61 (d, 2H, J=8.91 Hz), 7.45 (s, 1H), 7.43 (d, 2H, J=8.91 Hz), 7.21-7.25 (m, 1H), 6.84-6.92 (m, 3H), 5.17 (s, 2H), 3.72-3.83 (m, 2H), 2.34 (m, 2H), 2.18 (s, 3H), 2.06 (m, 1H), 1.49-1.64 (m, 4H), 1.18 (m, 1H), 1.04 (s, 3H). MS (ESI+) 494.06 (M+1H+).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with MeOH

Sources & evidence

ORD record
ord-bc0848963f324e63a10d8a58a7974b65
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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