Water → HCID 178428256, compound

HRID 1897945Notes

Reaction equation

HRID 1897945 reaction equation
[Cl:1][C:2]1[C:3]([F:38])=[C:4]([CH:35]=[CH:36][CH:37]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[CH:24][N:23](COCC[Si](C)(C)C)[N:22]=3)[CH:17]=[C:16]([CH3:34])[N:15]=2)[CH2:9][CH2:8]1)=[O:6].O.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[Cl:1][C:2]1[C:3]([F:38])=[C:4]([CH:35]=[CH:36][CH:37]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[CH:24][NH:23][N:22]=3)[CH:17]=[C:16]([CH3:34])[N:15]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 66890990HCID 66890990, compound

Product 1

HCID 178428256HCID 178428256, compound

Conditions

Temperature
60 °C

Procedure

24.9 mg of 2-((1-(3-chloro-2-fluorobenzoyl)piperidin-4-yl)methyl)-6-methyl-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrimidin-4-amine was dissolved in 0.9 ml of trifluoroacetic acid and 0.1 ml of water at room temperature, followed by stirring the reaction mixture at 60° C. for 30 minutes. The reaction mixture was cooled to room temperature, and concentrated in vacuo. The reaction mixture was purified by a reversed phase preparative liquid chromatography, followed by concentrating the obtained fraction in vacuo to give the title compound as a white solid.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe reaction mixture was purified by a reversed phase preparative liquid chromatography
  5. concentrationby concentrating the obtained fraction in vacuo

Sources & evidence

ORD record
ord-0082909fe5b149678cf2793eccf24e19
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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