1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335438, compound

HRID 710627Notes

Reaction equation

HRID 710627 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:7]=[CH:6][N:5]([CH2:8][C:9]([OH:11])=O)[N:4]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:29]3[CH2:28][CH2:27][CH2:26][NH:25][C:24]=3[CH:23]=[N:22]2)=[CH:17][CH:16]=1>>[F:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[C:29]3[CH2:28][CH2:27][CH2:26][N:25]([C:9](=[O:11])[CH2:8][N:5]4[CH:6]=[N:7][C:3]([C:2]([F:1])([F:13])[F:12])=[N:4]4)[C:24]=3[CH:23]=[N:22]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 84034029[3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]acetic acid

Product 1

HCID 73335438HCID 73335438, compound

Procedure

The title compound was prepared from 2-(3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl)acetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 2× brine. The reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 33 mg of the title compound as a white solid. 1H NMR (400 MHz, CD3OD, mixture of rotamers) δ 8.41 (s, 1H), 8.35 (s, 0.75H), 7.60 (s, 0.25H), 7.43-7.50 (m, 2H), 7.15-7.23 (m, 2H), 5.41 (s, 0.5H), 5.30 (s, 1.5H), 3.94 (m, 0.5H), 3.84 (m, 1.5H), 2.89 (m, 2H), 2.15 (m, 1.5H), 2.07 (m, 0.5H); MS: (ES) m/z calculated for C17H15F4N6O [M+H]+ 395.1, found 395.1.

Workup

  1. washThe product mixture was washed with 2× brine
  2. customThe reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-db995c079691422f89f1b65e4e17355e
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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