1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine → HCID 73335540, compound

HRID 710632Notes

Reaction equation

HRID 710632 reaction equation
[Cl:1][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[N:4][N:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:34]3[CH2:33][CH2:32][CH2:31][NH:30][C:29]=3[CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[Cl:1][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[N:4][N:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([N:30]2[CH2:31][CH2:32][CH2:33][C:34]3[N:26]([C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=4)[N:27]=[CH:28][C:29]2=3)=[O:11])[C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridineHCID 86711673HCID 86711673, compound

Product 1

HCID 73335540HCID 73335540, compoundYield 74%

Procedure

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-3-methylbutanoic 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 2×1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 89 mg (74%) of the title compound as a glassy white solid. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 7.44 (m, 2H), 7.16 (m, 2H), 5.03 (d, J=10.9 Hz, 1H), 3.89 (ddd, J=2.7, 8.2, 10.9 Hz, 1H), 3.78 (ddd, J=2.7, 7.8, 10.9 Hz, 1H), 2.96 (m, 1H), 2.79 (m, 2H), 2.37 (s, 3H), 1.99 (m, 1H), 1.82 (m, 1H), 1.12 (d, J=6.3 Hz, 3H), 0.79 (d, J=7.1 Hz, 3H); MS: (ES) m/z calculated for C22H23ClF4N5O [M+H]+ 484.1, found 484.1.

Workup

  1. washThe product mixture was washed with 2×1 M NaHSO4
  2. customThe reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-acc86f1ee60045e391db990aa648850e
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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