(1,5-dimethyl-1H-pyrrol-2-yl)methanamine → 2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-((1,5-dimethyl-1H-pyrrol-2-yl)methyl)-4-methylthiazole-5-carboxamide

HRID 1887358Notes

Reaction equation

HRID 1887358 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[CH2:8][NH2:9].[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[S:25][C:26]([C:30](O)=[O:31])=[C:27]([CH3:29])[N:28]=2)[C:20](=[O:33])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[S:25][C:26]([C:30]([NH:9][CH2:8][C:3]3[N:2]([CH3:1])[C:6]([CH3:7])=[CH:5][CH:4]=3)=[O:31])=[C:27]([CH3:29])[N:28]=2)[C:20](=[O:33])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 737232(1,5-dimethyl-1H-pyrrol-2-yl)methanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 577445172-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-N-((1,5-dimethyl-1H-pyrrol-2-yl)methyl)-4-methylthiazole-5-carboxamideYield 33%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (1,5-dimethyl-1H-pyrrol-2-yl)methanamine in place of benzo[b]thiophen-2-ylmethanamine to react with 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 33% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.60 (d, J=8.1 Hz, 1H), 8.53 (t, J=5.4 Hz, 1H), 7.44-7.33 (m, 5H), 6.37 (dd, J=8.1, 2.7 Hz, 1H), 6.21 (d, J=2.7 Hz, 1H), 5.91 (d, J=3.3 Hz, 1H), 5.64-5.63 (m, 1H), 5.15 (s, 2H), 4.32 (d, J=5.4 Hz, 2H), 3.39 (s, 3H), 2.51 (s, 3H), 2.10 (s, 3H); MS (ES+) m/z 449.2 (M+1).

Sources & evidence

ORD record
ord-e5e9fd3f80a14150b8fddd1e94ee31a6
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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