Pyridine → 1-{[5-(4-fluorophenyl)-1H-pyrazol-4-yl]carbonyl}-5-methyl-3-phenylpyrrolidin-3-ol

HRID 1446344Notes

Reaction equation

N1C=CC=CC=1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][N:17]=[CH:16][C:15]=2[C:19]([OH:21])=O)=[CH:10][CH:9]=1.[CH3:22][CH:23]1[NH:27][CH2:26][C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([OH:28])[CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[NH:18][N:17]=[CH:16][C:15]=2[C:19]([N:27]2[CH:23]([CH3:22])[CH2:24][C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([OH:28])[CH2:26]2)=[O:21])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Pyridine (13 μL, 0.16 mmol, 4 equ.) was added to a solution of 5-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid (8 mg, 0.04 mmol), 5-methyl-3-phenylpyrrolidin-3-ol (7 mg, 0.04 mmol) and TBTU (15 mg, 0.048 mmol, 1.2 equ.) in DMF (0.3 mL) at rt. The reaction mixture was stirred at 60° C. overnight. The crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (3 mg). MS (ESI, pos. ion) m/z: calcd for C21H20FN3O2: 365.1540, found 365.1541.

Workup

customThe crude product was purified by RP-HPLC
customAfter evaporation of the solvents the product
customwas dried in vacuum

Sources & evidence

ORD record: ord-f7220aeeddea4bdaa05c08db8d04df47
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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