Hydrochloric Acid → 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetic acid

HRID 58088Notes

Reaction equation

HRID 58088 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][C:18]([O:20]CC)=[O:19])[CH:16]=2)[CH:4]=1.[OH-].[Li+].[ClH:27]>C1COCC1.O>[ClH:27].[F:23][C:2]([F:1])([F:24])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][NH:9]2)=[C:5]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][C:18]([OH:20])=[O:19])[CH:16]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117772858ethyl 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetate

Product 2

HCID 313Hydrochloric AcidHCID 897830682-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a mixture of ethyl 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetate (0.14 g, 0.414 mmol) and THF—H2O (5:1, 4 mL) was added lithium hydroxide (0.621 mL, 1.242 mmol) at room temperature. The reaction mixture was stirred for 1 hour, then acidified with concentrated HCl, and concentrated in vacuo to give an HCl salt of the title compound as a light brown solid (0.12 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.97 (s, 2H), 7.58 (s, 1H), 7.76 (s, 1H), 8.22 (s, 1H), 8.54 (s, 1H), 8.59 (s, 1H), 13.70 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C13H9F3N4O2, 311.1. found 311.15.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06a25a6304e844048634dde31ec0299b
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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