N,N'-Dimethylethylenediamine → 4-Fluoro-N-{[2-oxo-6-(1H-1,2,4-triazol-1-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide

HRID 1878028노트

반응식

HRID 1878028 반응식
I[C:2]1[CH:3]=[CH:4][C:5]2[N:10](CC3C=CC(OC)=CC=3)[C:9](=[O:20])[O:8][C:7]([CH2:25][NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)([C:21]([F:24])([F:23])[F:22])[C:6]=2[CH:36]=1.[NH:37]1[CH:41]=[N:40][CH:39]=[N:38]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:27]([NH:26][CH2:25][C:7]2([C:21]([F:22])([F:23])[F:24])[C:6]3[CH:36]=[C:2]([N:37]4[CH:41]=[N:40][CH:39]=[N:38]4)[CH:3]=[CH:4][C:5]=3[NH:10][C:9](=[O:20])[O:8]2)=[O:35])=[CH:29][CH:30]=1

참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 92571H-1,2,4-TriazoleHCID 62657Potassium Phosphate, TribasicHCID 44549927N-{[6-iodo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide

생성물 1

HCID 445503754-Fluoro-N-{[2-oxo-6-(1H-1,2,4-triazol-1-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

A solution of N-{[6-iodo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (50 mg, 0.081 mmol), 1,2,4-triazole (16.9 mg, 0.244 mmol), potassium phosphate (25.9 mg, 0.122 mmol), N,N′-dimethylethylenediamine (6.9 μL, 0.065 mmol) and copper iodide (I) (3.1 mg, 0.016 mmol) in DMF (0.4 mL) was stirred for 1 hour under heating at 110° C. The temperature of the solution was brought to room temperature, and the solution was diluted with ethyl acetate, which was washed sequentially with a saturated aqueous ammonium chloride solution and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was subjected to the same condition as in Example 154 to effect deprotection of the 4-methoxybenzyl group, whereby the objective compound (8.0 mg, 23%) was obtained as a pale white solid.

후처리

  1. customwas brought to room temperature
  2. washwas washed sequentially with a saturated aqueous ammonium chloride solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the drying agent was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customwas obtained as a pale white solid

출처 및 근거

ORD 기록
ord-71d299347fea4b629b89c9bad2ebbd4d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314094B2

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