Hydrochloric Acid → HCID 86597719, compound

HRID 547836Notes

Reaction equation

HRID 547836 reaction equation
[F:1][C:2]([F:53])([F:52])[C:3]1[CH:4]=[C:5]([C:13]([CH3:51])([CH3:50])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:39]3[CH2:44][CH2:43][N:42]([S:45]([CH3:48])(=[O:47])=[O:46])[C@@H:41]([CH3:49])[CH2:40]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30](C)(C)[O:31][SiH2]C(C)(C)C)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:50])([CH3:51])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:39]3[CH2:44][CH2:43][N:42]([S:45]([CH3:48])(=[O:47])=[O:46])[C@@H:41]([CH3:49])[CH2:40]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][OH:31])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:52])[F:53])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178461495HCID 178461495, compound

Product 1

HCID 86597719HCID 86597719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 73 mg (0.093 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-6-((S)-4-methanesulfonyl-3-methyl-piperazin-1-yl)-pyridin-3-yl]-N-methyl-isobutyramide in 5 ml of a 1 M solution of hydrochloric acid in methanol was stirred at room temperature. Conversion was monitored by thin layer chromatography. After complete consumption of the starting material the reaction mixture was diluted with a 1 M aqueous solution of sodium hydroxide and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 62 mg (quantitative) of the title compound as a light yellow solid.

Workup

  1. customAfter complete consumption of the starting material the reaction mixture
  2. additionwas diluted with a 1 M aqueous solution of sodium hydroxide
  3. extractionextracted with three portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-056565c899dc4b9e9e5528f794a73c42
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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