α-Ethyl-5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid → HCID 73335637, compound

HRID 710637Notes

Reaction equation

HRID 710637 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH:29]([CH3:33])[NH:28][C:27]=3[CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:32]3[CH2:31][CH2:30][CH:29]([CH3:33])[N:28]([C:8](=[O:10])[CH:7]([N:6]4[C:2]([CH3:1])=[CH:3][C:4]([C:13]([F:16])([F:15])[F:14])=[N:5]4)[CH2:11][CH3:12])[C:27]=3[CH:26]=[N:25]2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 19576698α-Ethyl-5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-acetic acidHCID 67984606HCID 67984606, compound

Product 1

HCID 73335637HCID 73335637, compoundYield 46%

Procedure

The title compound was prepared from 2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)butanoic acid and 1-(4-fluorophenyl)-5-methyl-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 13 mg (46%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.40 (s, 1H), 7.47 (m, 2H), 7.16 (m, 2H), 6.35 (s, 1H), 5.37 (dd, J=6.7, 8.6 Hz, 1H), 4.63 (m, 1H), 2.86 (m, 1H), 2.73 (ddd, J=1.9, 5.1, 11.3 Hz, 1H), 2.37 (s, 3H), 2.27 (m, 2H), 1.92-1.97 (m, 2H), 0.93 (t, J=6.5 Hz, 3H), 0.57 (t, J=6.7 Hz, 3H); MS: (ES) m/z calculated for C22H24F4N5O [M+H]+ 450.2, found 450.2.

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-753dcb3d0cc9421ea4c28a2e9045d0e5
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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