Lithium Hydroxide → HCID 72706744, compound

HRID 595263Notes

Reaction equation

HRID 595263 reaction equation
[Li+].[OH-].[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[N:23][N:24]([CH:26]([CH3:31])[C:27]([O:29]C)=[O:28])[CH:25]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=2)[CH:9]=1>CO.O>[CH3:3][C:4]1[CH:5]=[C:6]([C:21]2[CH:22]=[N:23][N:24]([CH:26]([CH3:31])[C:27]([OH:29])=[O:28])[CH:25]=2)[CH:7]=[C:8]([NH:10][C:11]2[N:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][N:12]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 118208426HCID 118208426, compound

Product 1

HCID 72706744HCID 72706744, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

LiOH (10.6 mg, 0.44 mmol) was added to a solution of methyl 2-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanoate (18 mg, 0.04 mmol) in methanol (870 μL) and water (87 μL). The reaction mixture was allowed to stir at room temperature for 3 hours then concentrated using under reduced pressure. The residue was purified by reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford 2-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]propanoic acid. MS ESI calcd. for C18H17F3N5O2[M+H]+ 392. found, 392. 1H NMR (500 MHz, DMOS-d6) δ 13.04 (s, 1H), 10.11 (s, 1H), 8.80 (d, J=4.9, 1H), 8.12 (s, 1H), 7.84 (s, 1H), 7.75 (s, 1H), 7.32 (s, 1H), 7.24 (d, J=4.9, 1H), 7.09 (s, 1H), 5.11 (q, J=7.3, 1H), 2.29 (s, 3H), 1.67 (d, J=7.3, 3H).

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by reverse phase HPLC (ACN/water with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-315f482615b94c89b5818e433b45244b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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