HCID 67104051, compound → HCID 136174638, compound

HRID 930592Notes

Reaction equation

HRID 930592 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([N:12]2[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]2)=[C:6]([F:19])[CH:5]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[C:21]1[C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27]([CH2:34][C:35](O)=[O:36])[N:26]=1>>[Cl:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([N:12]2[CH2:17][CH2:16][N:15]([C:35](=[O:36])[CH2:34][N:27]3[C:28]4=[N:29][CH:30]=[CH:31][CH:32]=[C:33]4[C:25]([C:21]4[NH:20][CH:24]=[CH:23][N:22]=4)=[N:26]3)[C@@H:14]([CH3:18])[CH2:13]2)=[C:6]([F:19])[CH:5]=1

Participants

3

Reactant 2

HCID 67104051HCID 67104051, compoundHCID 1361746462-(3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid

Product 1

HCID 136174638HCID 136174638, compound

Procedure

The title compound was prepared following protocol A. (S)-1-(4-Chloro-2-fluoro-5-methoxy-phenyl)-3-methylpiperazine 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% MeOH in CH2Cl2) to provide 1-[(S)-4-(4-chloro-2-fluoro-5-methoxyphenyl)-2-methylpiperazin-1-yl]-2-[3-(1H-imidazol-2-yl)pyrazolo[3,4-b]pyridin-1-yl]ethanone as a tan solid (29 mg): 1H NMR (CDCl3, 400 MHz) δ □8.79 (dd, 1H), 8.55 (dd, 1H), 7.27-7.21 (m, 3H), 7.07 (d, 1H), 6.43 (br. d, 1H), 5.46-5.37 (m, 2H), 4.83 (br. s, 0.3H), 4.51-4.48 (m, 0.6H), 4.28-4.21 (m, 0.6H), 3.86 (s, 0.9H), 3.85 (s, 2.1H), 3.79 (br. s, 0.3H), 3.67 (br. s, 0.3H), 3.33-3.21 (m, 2.5H), 2.95-2.93 (m, 0.9H), 2.83-2.76 (m, 1.6H), 1.48-1.40 (m, 3H); LC/MS m/z (M+H)+ 484.4.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by silica gel chromatography (2% to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2ff4899aa4224feca41a3613aba36099
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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