(1h-indol-2-ylmethyl)amine → HCID 57744465, compound

HRID 1887365Notes

Reaction equation

HRID 1887365 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH2:11].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][N:23]([C:26]2[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22](=[O:35])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][NH:11][C:32]([C:28]1[S:27][C:26]([N:23]2[CH:24]=[CH:25][C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:21][C:22]2=[O:35])=[N:30][C:29]=1[CH3:31])=[O:33]

Participants

3

Reactant 2

HCID 582331(1h-indol-2-ylmethyl)amineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744465HCID 57744465, compoundYield 22%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (1H-indol-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 22% yield: 1H NMR (300 MHz, DMSO-d6) δ 10.91 (s, 1H), 8.73 (t, J=5.6 Hz, 1H), 8.62 (d, J=8.1 Hz, 1H), 7.45-7.29 (m, 7H), 7.01-6.87 (m, 2H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.25-6.22 (m, 2H), 5.16 (s, 2H), 4.53 (d, J=5.6 Hz, 2H), 2.56 (s, 3H); MS (ES+) m/z 471.2 (M+1).

Sources & evidence

ORD record
ord-cf2b10065b6b430eb55522dddca96b16
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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