2-(2-Chloro-4-hydroxy-phenyl)-N-methyl-acetamide → 2-{2-Chloro-4-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-phenyl}-N-methyl-acetamide

HRID 1272059Notes

Reaction equation

HRID 1272059 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[Cl:17][C:18]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:19]=1[CH2:25][C:26]([NH:28][CH3:29])=[O:27]>>[Cl:17][C:18]1[CH:23]=[C:22]([O:24][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=4)[S:10][C:3]=23)[CH:21]=[CH:20][C:19]=1[CH2:25][C:26]([NH:28][CH3:29])=[O:27]

Participants

3

Reactant 2

HCID 184565782-(2-Chloro-4-hydroxy-phenyl)-N-methyl-acetamideHCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

Product 1

HCID 184565702-{2-Chloro-4-[2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridin-7-yloxy]-phenyl}-N-methyl-acetamide

Procedure

was prepared from coupling of 7-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine and intermediate 63a following Method C. 1H NMR (300 MHz, CD3OD) δ 8.38 (d, 1H, J=5.65 Hz), 7.67 (s, 1H), 7.38 (d, 1H, J=8.48 Hz), 7.27 (d, 1H, J=2.44 Hz), 7.20 (s, 1H), 7.12–7.06 (m, 1H), 6.99 (s, 1H), 6.67 (d, 1H, J=5.47 Hz), 3.91 (s, 3H), 3.61(s, 2H), 2.66 (s, 3H). LCMS (ESI+) [M+H]/z Calc'd 413, found 413. Anal. (C20H17N4O2SCl.0.25CH2Cl2), C, H, N.

Sources & evidence

ORD record
ord-192d4ca274ca4395b0766b98cd5162c5
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

Loading…