Lithium Hydroxide → HCID 86592795, compound

HRID 1245124Notes

Reaction equation

HRID 1245124 reaction equation
C[O:2][C:3](=[O:37])[CH:4]([NH:18][C:19]([C:21]1[CH:22]=[N:23][N:24]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:25]=1[C:26]([F:29])([F:28])[F:27])=[O:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-].C1(C2C=CC=CC=2)C=CC(CC(NC(C2C=NN(C3C=CC(F)=CC=3)C=2[C:59]([F:62])([F:61])[F:60])=O)C(O)=O)=CC=1>C1COCC1>[F:36][C:33]1[CH:34]=[CH:35][C:30]([N:24]2[C:25]([C:26]([F:27])([F:29])[F:28])=[C:21]([C:19]([NH:18][C@@H:4]([CH2:5][C:6]3[CH:7]=[CH:8][C:9]([C:12]4[CH:13]=[CH:14][C:15]([C:59]([F:62])([F:61])[F:60])=[CH:16][CH:17]=4)=[CH:10][CH:11]=3)[C:3]([OH:2])=[O:37])=[O:20])[CH:22]=[N:23]2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21921308HCID 21921308, compoundHCID 69610327HCID 69610327, compound

Product 1

HCID 86592795HCID 86592795, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (0.200 g, 0.731 mmol, prepared in example 635) in DMF (4.0 mL) was reacted with 2-L-amino-3-biphenyl-4-yl-propionic acid methyl ester hydrochloride (0.213 g, 0.731 mmol), HBTU (0.277 g, 0.731 mmol), and DIEA (0.450 mL, 2.566 mmol) as described in general procedure A. The crude compound was purified by flash column chromatography on silica gel using CHCl3 (+10% hexane) to give 0.150 g (41%) of 3-biphenyl-4-yl-2-{[1-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-propionic acid methyl ester. A solution of this ester (0.085 g, 0.166 mmol) in THF (3.0 mL) was treated with LiOH (0.025 g) by general procedure I to afford (0.070 g, 85%) of the title compound 3-Biphenyl-4-yl-2-{[1-(4-fluoro-phenyl)-5-trifluoromethyl-1H-pyrazole-4-carbonyl]-amino}-propionic acid as a white solid. LCMS: 498 (M+1)+. 1H NMR (DMSO-d6) 8.94 [d, 1H], 8.08 [s, 1H], 7.58 [m, 6H], 7.42 [m, 7H], 4.63 [m, 1H], 3.22 [m, 1H], 3.04 [m, 1H].

Sources & evidence

ORD record
ord-c03eee74d6b34658bafd07c638afe82f
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

Loading…