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

HRID 1446345Notes

Reaction equation

[CH3:1][CH:2]1[NH:6][CH2:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([OH:7])[CH2:3]1.C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[NH:33][N:32]=[CH:31][C:30]=2[C:34](O)=[O:35])=[CH:25][CH:24]=1.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CN(C=O)C>[CH3:21][O:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[NH:33][N:32]=[CH:31][C:30]=2[C:34]([N:6]2[CH:2]([CH3:1])[CH2:3][C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([OH:7])[CH2:5]2)=[O:35])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 5-methyl-3-phenylpyrrolidin-3-ol (9 mg, 0.05 mmol) and triethylamine (28 μL, 0.2 mmol, 4 equ.) in DMF (0.2 mL) was added to a solution of 5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylic acid (11 mg, 0.05 mmol, 1.2 equ.) and 1-propanephosphonic acid cyclic anhydride (70 μL, 0.115 mmol, 2.3 equ., 50% solution in ethyl acetate) in DMF (0.1 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 C22H23N3O3: 377.1739, found 377.1739.

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-fffac76fcd7a4724a38d69f31ce1532f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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