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Methylamine → N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-3-(2-methylamino-pyrimidin-4-yloxy)-benzamide

HRID 1028449
Notes
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Reaction equation

HRID 1028449 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]([O:29][CH3:30])=[C:9]([NH:11][C:12](=[O:28])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:14]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:8]([O:29][CH3:30])=[C:9]([NH:11][C:12](=[O:28])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([O:20][C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:37][CH3:36])[N:22]=3)[CH:14]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86664518N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyrimidin-4-yloxy)-4-methyl-benzamide

Product 1

HCID 46181755N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-3-(2-methylamino-pyrimidin-4-yloxy)-benzamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A mixture of 200 mg N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyrimidin-4-yloxy)-4-methyl-benzamide and 2 ml of a 2 M methylamine solution in tetrahydrofuran is stirred overnight at ambient temperature in a closed microwave glass container. For working up the reaction mixture is diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride solution, dried on magnesium sulphate and evaporated down. The crude product is chromatographed on a silica gel column with ethyl acetate/cyclohexane (50:50→100:0) as eluant.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. customdried on magnesium sulphate
  3. customevaporated down
  4. customThe crude product is chromatographed on a silica gel column with ethyl acetate/cyclohexane (50:50→100:0) as eluant

Sources & evidence

ORD record
ord-c12287e5b5174597a0541a35e2b933a3
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes