1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 86711669, compound

HRID 710628Notes

Reaction equation

HRID 710628 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=O)[N:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[N:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[CH2:29][CH2:28][CH2:27][NH:26][C:25]=3[CH:24]=[N:23]2)=[CH:18][CH:17]=1>C(Cl)(Cl)Cl>[F:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:30]3[CH2:29][CH2:28][CH2:27][N:26]([C:8](=[O:10])[CH2:7][N:6]4[C:2]([CH3:1])=[N:3][C:4]([C:11]([F:14])([F:13])[F:12])=[N:5]4)[C:25]=3[CH:24]=[N:23]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 86711670HCID 86711670, compound

Product 1

HCID 86711669HCID 86711669, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared from 2-(5-methyl-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 diluted with 1 mL of CHCl3 and washed with H2O. The organic layer was concentrated and the residue was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 37 mg of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.34 (s, 0.8H), 7.59 (s, 0.2H), 7.44-7.50 (m, 2H), 7.14-7.27 (m, 2H), 5.29 (s, 0.4H), 5.18 (s, 1.6H), 3.93 (m, 0.4H), 3.86 (m, 1.6H), 2.88 (m, 2H), 2.56 (s, 2.4H), 2.55 (m, 0.6H), 2.14 (m, 1.6H), 2.06 (m, 0.4H); MS: (ES) m/z calculated for C18H17F4N6O [M+H]+ 409.1, found 409.1.

Workup

  1. washwashed with H2O
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-19946aa9f20a49f099bf7835fc8d80f3
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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