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

HRID 1028449Notes

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]

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-c12287e5b5174597a0541a35e2b933a3
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

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