(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid → HCID 73335634, compound

HRID 710635Notes

Reaction equation

HRID 710635 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4][N:5]([CH2:8][C:9]([OH:11])=O)[C:6]=1[CH3:7].[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N:24]1[C:32]2[CH2:31][CH2:30][CH2:29][NH:28][C:27]=2[CH:26]=[N:25]1>>[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[N:4][N:5]([CH2:8][C:9]([N:28]2[CH2:29][CH2:30][CH2:31][C:32]3[N:24]([C:18]4[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=4[F:16])[N:25]=[CH:26][C:27]2=3)=[O:11])[C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 1876853(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acidHCID 68041059HCID 68041059, compound

Product 1

HCID 73335634HCID 73335634, compoundYield 70%

Procedure

The compound was prepared 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid and 1-(2,4-difluorophenyl)-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 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 the title compound as a white foamy solid (47 mg, 70%). 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.39 (s, 0.8H), 7.64 (s, 0.2H), 7.48 (m, 2H), 7.00 (m, 2H), 5.25 (s, 0.4H), 5.14 (s, 1.6H), 3.92 (m, 0.4H), 3.85 (m, 1.6H), 2.70 (m, 2H), 2.33 (s, 2.4H), 2.32 (s, 0.6H), 2.11 (m, 1.6H), 2.03 (m, 0.4H); MS: (ES) m/z calculated for C19H16ClF5N5O [M+H]+ 460.1, found 460.1.

Workup

  1. washThe product mixture was washed with 2×1 M NaHSO4
  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-dcd4f33f2a65490b9b4936f8d51c63fd
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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