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

HRID 1272058Notes

Reaction equation

HRID 1272058 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]3)=[O:12])[S:10][C:3]=12.[Cl:19][C:20]1[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:21]=1[CH2:27][C:28]([NH:30][CH3:31])=[O:29]>>[Cl:19][C:20]1[CH:25]=[C:24]([O:26][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]([N:13]4[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14]4)=[O:12])[S:10][C:3]=23)[CH:23]=[CH:22][C:21]=1[CH2:27][C:28]([NH:30][CH3:31])=[O:29]

Participants

3

Reactant 2

HCID 184565782-(2-Chloro-4-hydroxy-phenyl)-N-methyl-acetamideHCID 22143479(7-Chloro-thieno[3,2-b]pyridin-2-yl)-(3-hydroxy-pyrrolidin-1-yl)-methanone

Product 1

HCID 588474602-{2-Chloro-4-[2-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-thieno[3,2-b]pyridin-7-yloxy]-phenyl}-N-methyl-acetamide

Procedure

was prepared from coupling of (7-chloro-thieno[3,2-b]pyridin-2-yl)-(3-hydroxy-pyrrolidin-1-yl)-methanone (2b) with intermediate 63a following Method C. 1H NMR (300 MHz, CD3OD) δ 8.45 (d, 1H, J=5.47 Hz), 7.84 (d, 1H, J=17.33 Hz), 7.40 (d, 1H, J=8.48 Hz), 7.29 (d, 1H, J=2.26 Hz), 7.13–7.08 (m, 1H), 6.74 (d, 1H, J=5.46 Hz), 4.42 (bs, 1H), 4.03–3.90 (m, 2H), 3.74–3.58(m, 5H), 2.66 (s, 3H), 2.10–1.97(m, 2H). LCMS (ESI+) [M+H]/z Calc'd 446, found 446. Anal. (C21H20N3O4SCl.0.7CH2Cl2), C, H, N.

Sources & evidence

ORD record
ord-49883559922f40c09e87eb6fc8e3ef55
Source dataset
uspto-grants-2007_04
Patent number
US07208500B2

Reaction notes

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