Water → HCID 178422978, 화합물

HRID 473165

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HRID 473165 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:12][C:13]([F:24])([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1)[C:14]([O-])=O.[Na+].C[Si](OP(=O)=O)(C)C.O>CCOC(C)=O>[F:24][C:13]([F:12])([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=1)[C:14]1[N:6]=[C:4]([OH:5])[C:3]2[C:2](=[CH:10][C:9]([CH3:11])=[CH:8][CH:7]=2)[N:1]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 28014742-Amino-4-methylbenzamideHCID 16133246Trimethyl(phosphooxy)silaneHCID 66609989Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

생성물 1

HCID 178422978HCID 178422978, 화합물수율 66.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

To a mixture of 2-amino-4-methylbenzamide (804 mg, 5.36 mmol) and sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate from Example 2 Step B (1.25 g, 5.89 mmol) was added trimethylsilyl polyphosphate (ca. 10 mL) and the mixture was heated at 130° C. in a sand bath overnight. The mixture was allowed to cool to rt, and then water (75 mL) and EtOAc (75 mL) were added and the mixture was stirred at rt for 1 h. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-60% EtOAc/hexanes to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-7-methylquinazolin-4-ol (1.09 g, 66%). LCMS (ESI) m/z 306 (M+H)+.

후처리

  1. temperatureto cool to rt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-60% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-1aca565682e64f6b9c259285947cf1cb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633207B2

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