Pyrrolidine → HCID 57940683, compound

HRID 1437294Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25](S(C)(=O)=O)[CH:24]=[CH:23][N:22]=3)[N:18]([C:31]3[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:20]=[C:19]([C:21]3[CH:26]=[C:25]([N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)[CH:24]=[CH:23][N:22]=3)[N:18]([C:31]3[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 57940688HCID 57940688, compound

Product 1

HCID 57940683HCID 57940683, compoundYield 96%

Procedure

A solution of 4-[1-(6-methoxy-3-pyridyl)-5-(4-methylsulfonyl-2-pyridyl)pyrazole-3-carbonyl]piperazine-1-carboxylic acid tert-butyl ester (0.186 g) obtained in Example 48 in pyrrolidine (3.7 mL) was stirred at 100° C. for 17 hours, and then the mixture was cooled in air. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as a solid (0.176 g, 96%).

Workup

temperaturethe mixture was cooled in air
customThe reaction mixture was partitioned between water and ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate anhydrate
filtrationAfter filtration
customthe solvent was removed under reduced pressure
customThe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record: ord-b41f01257d5640d9a604498ab5593942
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622471B2

Reaction notes

Loading…