2-(Aminomethyl)-5-methylpyrazine → HCID 57744511, compound

HRID 1887352Notes

Reaction equation

HRID 1887352 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.[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:5]3[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=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 27564962-(Aminomethyl)-5-methylpyrazineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744511HCID 57744511, compoundYield 42%

Procedure

Following the procedure as described in Example 22, making variation only as required to use (5-methylpyrazin-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 42% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.83 (t, J=5.7 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 8.44 (s, 2H), 7.48-7.31 (m, 5H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.48 (d, J=5.7 Hz, 2H), 2.54 (m, 3H), 2.43 (s, 3H); MS (ES+) m/z 448.2 (M+1).

Sources & evidence

ORD record
ord-eebb1b9811de4d4dbf176721b25f74d5
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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