Trifluoroacetic acid → (4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930383노트

반응식

HRID 930383 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C@:10]2([CH3:28])[CH2:15][C@@H:14]([C:16]([F:19])([F:18])[F:17])[O:13][C:12]([NH:20]C(=O)OC(C)(C)C)=[N:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([C@:10]2([CH3:28])[CH2:15][C@@H:14]([C:16]([F:18])([F:19])[F:17])[O:13][C:12]([NH2:20])=[N:11]2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 86732211tert-Butyl ((4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate

생성물 1

HCID 86732212(4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine수율 83.1%

실험 절차

tert-Butyl ((4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (0.56 g, 1.196 mmol) was treated with trifluoroacetic acid, 99% (10 ml, 135 mmol) and the mixture was stirred at room temperature for 15 min. The solvent was removed and the residue was worked up with saturated sodium bicarbonate solution and extracted with dichloromethane three times. The combined organic layers were dried on sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using a gradient of 10-60% EtOAc/hexane to give (4S,6S)-4-(5-bromo-2-methoxypyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (0.366 g, 0.994 mmol, 83% yield).

후처리

  1. customThe solvent was removed
  2. extractionextracted with dichloromethane three times
  3. customThe combined organic layers were dried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography

출처 및 근거

ORD 기록
ord-1ffa701ff67d4e19b9ddc45add725488
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296734B2

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