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4-Methoxypiperidine → N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide

HRID 930328
ノート
印刷プレビュー

反応式

HRID 930328 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C@:8]2([CH3:27])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:9]2)[CH:7]=1.Cl[C:30](OC1C=CC([N+]([O-])=O)=CC=1)=[O:31].[CH3:42][O:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>ClCCl>[C:19]([NH:18][C:10]1[O:11][C@H:12]([C:14]([F:17])([F:15])[F:16])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30]([N:47]3[CH2:48][CH2:49][CH:44]([O:43][CH3:42])[CH2:45][CH2:46]3)=[O:31])[CH:3]=[CH:4][C:5]=2[F:28])([CH3:27])[N:9]=1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 776664-MethoxypiperidineHCID 821294-Nitrophenyl chloroformateHCID 86732123N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

生成物 1

HCID 86732157N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide収率 61.1%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a cooled (0° C.) solution of N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (4l, 0.200 g, 0.506 mmol) in dichloromethane (4 mL) was added 4-nitrophenyl chloroformate (0.111 g, 0.551 mmol) as a solid. After 10 min the reaction was allowed to warm to room temperature. After 3 h 4-methoxy-piperidine (0.100 mL, 1.036 mmol) was added dropwise via syringe and the reaction was stirred overnight. The reaction was evaporated onto silica gel and purified by flash chromatography (Isco, 25 g) eluting with (25% EtOH/EtOAc):hexanes (0:1→2:3) to give N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide (166 mg. 61% yield) of a clear, colorless tar. MS m/z=537 [M+H]+. Calculated for C26H28F4N4O4: 536

後処理

  1. customThe reaction was evaporated onto silica gel
  2. custompurified by flash chromatography (Isco, 25 g)
  3. washeluting with (25% EtOH/EtOAc)

出典と根拠

ORDレコード
ord-a419775cb47b47b9a22e3166984f357a
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296734B2

反応ノート

読み込み中…

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