Triethylamine → [Bis-(4-methoxy-phenyl)-phenyl-methyl]-((R)-4-(6-bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-amine

HRID 1752462노트

반응식

HRID 1752462 반응식
[Br:1][C:2]1[N:7]=[C:6]([C@:8]2([CH3:19])[C:13]([F:15])([F:14])[C:12]([CH3:17])([CH3:16])[O:11][C:10]([NH2:18])=[N:9]2)[C:5]([F:20])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:51]=[CH:50][C:33]([C:34](Cl)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)=[CH:32][CH:31]=1>ClCCl>[CH3:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([C:34]([NH:18][C:10]2[O:11][C:12]([CH3:16])([CH3:17])[C:13]([F:14])([F:15])[C@:8]([C:6]3[C:5]([F:20])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)([CH3:19])[N:9]=2)([C:33]2[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:40][CH:39]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 86689146(R)-4-(6-Bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine

생성물 1

HCID 86689147[Bis-(4-methoxy-phenyl)-phenyl-methyl]-((R)-4-(6-bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-amine수율 102.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-4-(6-bromo-3-fluoro-pyridin-2-yl)-5,5-difluoro-4,6,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (106 mg, 0.301 mmol) and triethylamine (60.9 mg, 0.602 mmol) in dichloromethane (3 ml) was added solid 4,4′-dimethoxytrityl chloride (112 mg, 0.331 mmol) under argon atmosphere. The green solution was stirred at rt for 2 hrs and was then evaporated in vacuo. The crude product was taken up with ethyl acetate and washed with aqueous sodium bicarbonate solution, water and brine. The organic phase was dried over sodium sulfate, filtered and evaporated. Filtration over silica gel (4.4 g, toluene/ethyl acetate 6:4) afforded the title compound as a blue-gray foam (202 mg, 96%).

후처리

  1. customwas then evaporated in vacuo
  2. washwashed with aqueous sodium bicarbonate solution, water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. filtrationFiltration over silica gel (4.4 g, toluene/ethyl acetate 6:4)

출처 및 근거

ORD 기록
ord-5945784eba7f49e99ca3410b949990b5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163011B2

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