(4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid → HCID 73335334, compound

HRID 710622Notes

Reaction equation

HRID 710622 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]=[CH:21][C:20]([N:23]2[C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[C:25]([CH3:32])=[N:24]2)=[CH:19][CH:18]=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:27]2[CH2:28][CH2:29][CH2:30][C:31]3[N:23]([C:20]4[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=4)[N:24]=[C:25]([CH3:32])[C:26]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 67985123HCID 67985123, compound

Product 1

HCID 73335334HCID 73335334, compoundYield 41%

Procedure

The title compound was prepared from 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid and 1-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 75 mg (41%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 7.47 (m, 0.8H), 7.40 (m, 1.2H), 7.14 (m, 2H), 5.11 (s, 1.2H), 5.01 (s, 0.8H), 3.81 (m, 2H), 2.85 (m, 2H), 2.29-2.40 (m, 6H), 2.07 (m, 2H); MS: (ES) m/z calculated for C20H19ClF4N5O [M+H]+ 456.1, found 456.1.

Workup

  1. washThe product mixture was washed with 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-ded3de73545a4424bd767a5670cf9945
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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