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Ammonia → 4-[4-Chloro-2-((S)-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide

HRID 240623
Notes
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Reaction equation

HRID 240623 reaction equation
CO[C:3]([C:5]1[S:34][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[O:21][C@H:22]3[CH2:27][CH2:26][CH2:25][N:24](C(=O)C(F)(F)F)[CH2:23]3)[C:7]=2[C:6]=1[CH3:35])=[O:4].[NH3:36]>CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:12]2[C:7]3[C:6]([CH3:35])=[C:5]([C:3]([NH2:36])=[O:4])[S:34][C:8]=3[N:9]=[CH:10][N:11]=2)=[C:15]([O:21][C@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222AmmoniaHCID 584132164-{4-Chloro-2-[(S)-1-(2,2,2-trifluoro-acetyl)-piperidin-3-yloxy]-phenylamino}-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Product 1

HCID 584131444-[4-Chloro-2-((S)-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

4-{4-Chloro-2-[(S)-1-(2,2,2-trifluoro-acetyl)-piperidin-3-yloxy]-phenylamino}-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (150 mg) and ammonia in methanol (7M; 5 ml) were combined and heated at 100° C. in sealed tube. The reaction heated under these conditions for 48 h. The residue was purified by chromatography tho give the inteded product.

Workup

  1. temperatureThe reaction heated under these conditions for 48 h
  2. customThe residue was purified by chromatography
  3. customtho give the inteded product

Sources & evidence

ORD record
ord-345aec5582ec4f23bfbb98a83d6ad2ef
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648068B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes