1-Methyl-5-aminomethylimidazole → HCID 57744486, compound

HRID 1887359Notes

Reaction equation

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

Participants

Reactant 2

HCID 27954241-Methyl-5-aminomethylimidazole

HCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744486HCID 57744486, compoundYield 52%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (1-methyl-1H-imidazol-5-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 52% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.65-8.58 (m, 2H), 7.51 (s, 1H), 7.44-7.30 (m, 5H), 6.78 (s, 1H), 6.38 (dd, J=8.1, 2.6 Hz, 1H), 6.22 (d, J=2.6 Hz, 1H), 5.15 (s, 2H), 4.36 (d, J=5.3 Hz, 2H), 3.58 (s, 3H), 2.52 (s, 3H); MS (ES+) m/z 436.2 (M+1).

Sources & evidence

ORD record: ord-b5acf3ed46324a609042a1c3d8019865
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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