Methylamine → 6-(2-Methylamino-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 556348Notes

Reaction equation

HRID 556348 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=4)=[CH:20][C:15]=3[O:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:31][NH2:32]>C1COCC1.O.CCOC(C)=O>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21][C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:32][CH3:31])[N:23]=4)=[CH:20][C:15]=3[O:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 247626256-(2-Chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Product 1

HCID 247626276-(2-Methylamino-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 mg (0.115 mMol) 6-(2-chloro-pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide are dissolved in 5 ml THF. Then 250 μl methylamine (2 M in THF; 0.50 mMol) are added and the solution is stirred in a sealed tube for 20 h. The mixture is diluted with water and EtOAc, the aq. layer separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (reversed phase; Gilson) gives the title compound: MS: [M+1]+=430; HPLC: tRet=14.0.

Workup

  1. customthe aq. layer separated off
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c576facd39fd4508a7f9c180ffdfd875
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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