1-[4-Chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]-piperazine dihydrochloride → 1-{4-[4-chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]piperazin-1-yl}-2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]ethanone

HRID 390566Notes

Reaction equation

HRID 390566 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([O:10][CH2:11][CH2:12][F:13])=[CH:8][C:7]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:6]([F:20])[CH:5]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[C:22]1[C:26]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH2:35][C:36](O)=[O:37])[N:27]=1>>[Cl:3][C:4]1[C:9]([O:10][CH2:11][CH2:12][F:13])=[CH:8][C:7]([N:14]2[CH2:15][CH2:16][N:17]([C:36](=[O:37])[CH2:35][N:28]3[C:29]4=[N:30][CH:31]=[CH:32][CH:33]=[C:34]4[C:26]([C:22]4[NH:21][CH:25]=[CH:24][N:23]=4)=[N:27]3)[CH2:18][CH2:19]2)=[C:6]([F:20])[CH:5]=1

Participants

3

Reactant 2

HCID 866189161-[4-Chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]-piperazine dihydrochlorideHCID 1361746462-(3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid

Product 1

HCID 1358822801-{4-[4-chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]piperazin-1-yl}-2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]ethanone

Procedure

The title compound was prepared following Protocol A. 1-[4-Chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]-piperazine dihydrochloride and [3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]acetic acid were used as the coupling components. The crude product was purified by silica gel chromatography (2% to 3.5% MeOH in CH2Cl2) to provide 1-{4-[4-chloro-2-fluoro-5-(2-fluoroethoxy)phenyl]piperazin-1-yl}-2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]ethanone as a tan solid: 1H NMR (CDCl3, 400 MHz) δ 8.79 (dd, 0.6; H, J=8.0, 1.8 Hz), 8.67 (d, 0.4; H, J=6.4 Hz), 8.57-8.55 (m, 1H), 7.30-7.25 (m, 1H), 7.11-7.06 (m, 2H), 6.63 (d, 0.6H, J=7.6 Hz), 6.57 (d, 0.4H, J=7.6 Hz), 6.54 (d, 1H, J=7.6 Hz), 5.45 (s, 0.7H), 5.43 (s, 1.3H), 4.83-4.80 (m, 1H), 4.71-4.68 (m, 1H), 4.31-4.18 (m, 2H), 3.82-3.76 (m, 3H), 3.50 (t, 1H, J=5.2 Hz), 3.23-3.04 (m, 4H); LC/MS m/z (M+H)+ 502.4.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by silica gel chromatography (2% to 3.5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d42ddf3cdbd245eaa62fed4fd24e0b80
Source dataset
uspto-grants-2013_02
Patent number
US08383630B2

Reaction notes

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