1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335541, compound

HRID 710633Notes

Reaction equation

HRID 710633 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][C:13]([OH:15])=O)[N:4]=1.[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][N:5]4[C:6]5=[N:7][CH:8]=[CH:9][CH:10]=[C:11]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 86711674HCID 86711674, compound

Product 1

HCID 73335541HCID 73335541, compound

Procedure

The title compound was prepared from 2-(3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-70% EtOAc in hexanes) to provide 58 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.65 (dd, J=2.6, 4.7 Hz, 1H), 8.32 (s, 0.8H), 8.24 (d, J=8.2 Hz, 1H), 7.72 (s, 0.2H), 7.44-7.52 (m, 2H), 7.33 (dd, J=4.3, 8.2 Hz, 1H), 7.13-7.23 (m, 2H), 5.76 (s, 0.4H), 5.65 (s, 1.6H), 3.93 (m, 2H), 2.89 (t, J=6.3 Hz, 2H), 2.17 (m, 1.6H), 2.06 (m, 0.4H); MS: (ES) m/z calculated for C21H17F4N6O [M+H]+ 445.1, found 445.1.

Workup

  1. customThe reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-acfd2458f12d42d68fb9b65ce602d2c8
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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