Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylate → HCID 24782249, compound

HRID 2239375Notes

Reaction equation

HRID 2239375 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[CH2:27][CH2:26][CH2:25][C@H:24]1[CH2:28][O:29][C:30]1[CH:31]=[C:32](CN)[CH:33]=[CH:34][CH:35]=1>>[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:34]4[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH2:28][C@@H:24]5[CH2:25][CH2:26][CH2:27][N:23]5[CH3:22])[CH:35]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 68707952HCID 68707952, compound

Product 1

HCID 24782249HCID 24782249, compound

Procedure

The title compound was synthesised using the same method as described for Example 20c using the reagents 5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.176 g, 0.55 mmol) and 1-(3-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}phenyl)methanamine (0.10 g, 0.45 mmol). Purification by prep-HPLC gave the product as a solid. Yield: 0.22 g (41%). 1H NMR (400 MHz, CD3OD) δ 8.08 (s, 1H), 7.58-7.64 (m, 2H), 7.38-7.46 (m, 3H), 7.21-7.27 (m, 1H), 6.82-6.94 (m, 3H), 5.17 (s, 2H), 3.90-3.99 (m, 1H), 3.79-3.87 (m, 1H), 3.03-3.13 (m, 1H), 2.54-2.66 (m, 1H), 2.43 (s, 3H), 2.22-2.32 (m, 1H), 1.92-2.06 (m, 1H), 1.64-1.88 (m, 3H). MS (ESI+) 466.12 (M+1H+).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-72a3c40cc9644412b12f1a968fea3e88
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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