Ethyl 5-(aminomethyl)furan-2-carboxylate → Ethyl 5-((2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamido)methyl)furan-2-carboxylate

HRID 1887364Notes

Reaction equation

HRID 1887364 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]([C:27]2[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23](=[O:36])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]([C:27]2[S:28][C:29]([C:33]([NH:1][CH2:2][C:3]3[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=3)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23](=[O:36])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 565895Ethyl 5-(aminomethyl)furan-2-carboxylateHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744485Ethyl 5-((2-(4-(Benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamido)methyl)furan-2-carboxylateYield 67%

Procedure

Following the procedure as described in Example 22, making variation only as required to use ethyl 5-(aminomethyl)furan-2-carboxylate 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 67% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.85 (t, J=5.6 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.45-7.33 (m, 5H), 7.20 (d, J=3.5 Hz, 1H), 6.45 (d, J=3.5 Hz, 1H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.45 (d, J=5.5 Hz, 2H), 4.23 (q, J=7.1 Hz, 2H), 2.54 (s, 3H), 1.24 (t, J=7.1 Hz, 3H); MS (ES+) m/z 494.2 (M+1).

Sources & evidence

ORD record
ord-a6c37ab4e5954695a63e6b21dc930d7d
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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