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 1752462ノート

反応式

HRID 1752462 の反応式
[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

参加物

5

反応物 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

生成物 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)-amine収率 102.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5945784eba7f49e99ca3410b949990b5
出典データセット
uspto-grants-2015_10
特許番号
US09163011B2

反応ノート

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