Dimethylformamide → HCID 58998957, compound

HRID 2105779Notes

Reaction equation

[CH:1]1([C:4]2NN=[C:6]([CH2:9][NH:10][C:11]([C:13]3[CH:17]=[C:16]([C:18]4[CH:23]=[C:22](OC)[CH:21]=[CH:20][C:19]=4OC)[N:15]([CH2:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[C:14]=3[CH3:35])=[O:12])[CH:5]=2)[CH2:3]C1.[C:36](=[O:39])([O-])[O-].[K+].[K+].[F:42][C:43]([F:47])([F:46])CI.[CH3:48]N(C=O)C>>[CH:9]1([NH:10][C:11]([C:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:39][CH2:36][C:43]([F:47])([F:46])[F:42])=[CH:20][C:19]=3[CH3:48])[N:15]([CH2:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[C:14]=2[CH3:35])=[O:12])[CH2:3][CH2:1][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 677091,1,1-Trifluoro-2-iodoethane

HCID 178492563HCID 178492563, compound

Product 1

HCID 58998957HCID 58998957, compound

Conditions

Temperature: 100 °C

Procedure

To 70 mg of 1-Cyclohexylmethyl-5-(4-hydroxy-2-methyl-phenyl)-2-methyl-1H-pyrrole-3-carboxylic acid cyclohexylamide (Example 111) in DMF was added 115 mg of potassium carbonate and 0.067 ml of 1,1,1-trifluoro-2-iodo-ethane. The reaction mixture was heated at 100° C. for 16 hours. The reaction mixture was then concentrated in vacuo and purified by column chromatography to give the title compound; MS (ISP) 491.3 (M+H)+.

Workup

concentrationThe reaction mixture was then concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-eaf6e463cf844de2b4d6f448146658c1
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579369B2

Reaction notes

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