Lithium Hydroxide → HCID 21921515, compound

HRID 1245122Notes

Reaction equation

HRID 1245122 reaction equation
C[O:2][C:3](=[O:42])[CH:4]([NH:23][C:24]([C:26]1[CH:27]=[N:28][N:29]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:30]=1[C:31]([F:34])([F:33])[F:32])=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-].FC1C=CC(N2C(C(F)(F)F)=C(C(NC(CC3C=CC(C4C=CC(C(F)(F)F)=CC=4)=CC=3)C(O)=O)=O)C=N2)=CC=1>C1COCC1>[F:41][C:38]1[CH:39]=[CH:40][C:35]([N:29]2[C:30]([C:31]([F:34])([F:33])[F:32])=[C:26]([C:24]([NH:23][CH:4]([CH2:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]4[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:14][CH:13]=4)=[CH:8][CH:7]=3)[C:3]([OH:42])=[O:2])=[O:25])[CH:27]=[N:28]2)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21921476HCID 21921476, compoundHCID 87913249HCID 87913249, compound

Product 1

HCID 21921515HCID 21921515, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of above acid in DMF (3.0 mL) was reacted with (2S)-amino-3-(4′-trifluoromethoxy-biphenyl-4-yl)-propionic acid methyl ester Hydrochloride (0.300 g, 0.797 mmol), HBTU (0.300 g, 0.797 mmol), and DIEA (0.425 mL, 2.40 mmol) as described in general procedure A. The crude compound was purified by flash column chromatography on silica gel using CHCl3 as the mobile phase to give 0.290 g (61%) of 2-{[1-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-3-(4′-trifluoromethoxy-biphenyl-4-yl)-propionic acid methyl ester. A solution of this ester (0.140 g, 0.235 mmol) in THF (4.0 mL) was treated with LiOH (0.035 g) by general procedure I to afford (0.125 g, 92%) of the title compound 2-{[1-(4-Fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-3-(4′-trifluoromethyl-biphenyl-4-yl)-propionic acid as a white solid. LCMS: 582 (M+1)+. 1H NMR (DMSO-d6) 8.94 [d, 1H], 8.07 [s, 1H], 7.76 [m, 2H], 7.57 [m, 4H], 7.42 [m, 6H], 4.64 [m, 1H], 3.22 [m, 1H], 3.05 [m, 1H].

Sources & evidence

ORD record
ord-dd5115482b4744f7bb5862be4482fd32
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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