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

HRID 1844617Notes

Reaction equation

HRID 1844617 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]

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 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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-b75d6789288a411fb824c9cc261e7d5c
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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