1-(1,3-Benzoxazol-2-yl)methanamine → N-(Benzo[d]oxazol-2-ylmethyl)-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

HRID 1887363Notes

Reaction equation

HRID 1887363 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N: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>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N: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 14155281-(1,3-Benzoxazol-2-yl)methanamineHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 57744484N-(Benzo[d]oxazol-2-ylmethyl)-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamideYield 44%

Procedure

Following the procedure as described in Example 22, making variation only as required to use benzo[d]oxazol-2-ylmethanamine 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 44% yield: 1H NMR (300 MHz, DMSO-d6) δ 9.01 (t, J=5.5 Hz, 1H), 8.62 (d, J=8.1 Hz, 1H), 7.72-7.64 (m, 2H), 7.45-7.31 (m, 7H), 6.40 (dd, J=8.1, 2.7 Hz, 1H), 6.24 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.68 (d, J=5.5 Hz, 2H), 2.57 (s, 3H); MS (ES+) m/z 473.1 (M+1).

Sources & evidence

ORD record
ord-4c0d9d361c504c788ee1e8416eb1fd3f
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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