1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335636, compound

HRID 710636Notes

Reaction equation

HRID 710636 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[N:4]=[C:5]([CH2:12][C:13]([OH:15])=O)[N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[C:33]3[CH2:32][CH2:31][CH2:30][NH:29][C:28]=3[CH:27]=[N:26]2)=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[C:33]3[CH2:32][CH2:31][CH2:30][N:29]([C:13](=[O:15])[CH2:12][C:5]4[N:6]5[CH:11]=[CH:10][CH:9]=[CH:8][C:7]5=[C:3]([C:2]([F:1])([F:17])[F:16])[N:4]=4)[C:28]=3[CH:27]=[N:26]2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 86711675HCID 86711675, compound

Product 1

HCID 73335636HCID 73335636, compoundYield 72%

Procedure

The title compound was prepared from 2-(1-(trifluoromethyl)imidazo[1,5-a]pyridin-3-yl)acetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method A. The reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 32 mg (72%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.36 (d, J=6.6 Hz, 1H), 8.35 (s, 0.9H), 8.06 (s, 0.1H), 7.63 (d, J=9.0 Hz, 1H), 7.50 (m, 0.3H), 7.42 (m, 1.7H), 7.12-7.22 (m, 2H), 7.01 (m, 1H), 6.79 (t, J=6.6 Hz, 1H), 4.51 (s, 0.2H), 4.38 (s, 1.8H), 4.08 (m, 1.7H), 3.90 (m, 0.3H), 2.86 (t, J=6.6 Hz, 0.3H), 2.80 (t, J=6.6 Hz, 1.7H), 2.02 (m, 2H); MS: (ES) m/z calculated for C22H18F4N5O [M+H]+ 444.1, found 444.1.

Workup

  1. customThe reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-71451b74a94949518e08c173f04bc40b
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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