2-Aminoindane → HCID 57744476, compound

HRID 1887351Notes

Reaction equation

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

Participants

Reactant 2

HCID 763102-Aminoindane

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

Product 1

HCID 57744476HCID 57744476, compoundYield 27%

Procedure

Following the procedure as described in Example 22, making variation only as required to use 2,3-dihydro-1H-inden-2-amine 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 27% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.61 (d, J=8.1 Hz, 1H), 8.51 (d, J=7.0 Hz, 1H), 7.50-7.31 (m, 5H), 7.20-7.09 (m, 4H), 6.38 (dd, J=8.1, 2.7 Hz, 1H), 6.22 (d, J=2.7 Hz, 1H), 5.15 (s, 2H), 4.66-4.58 (m, 1H), 3.24-3.11 (m, 2H), 2.95-2.84 (m, 2H), 2.52 (s, 3H); MS (ES+) m/z 458.2 (M+1).

Sources & evidence

ORD record: ord-68d76c372d1048f7ac79d0dd8cad6a53
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

Loading…