1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide

HRID 930281ノート

反応式

HRID 930281 の反応式
C([NH:9][C:10]1[O:11][C@H:12]([C:36]([F:39])([F:38])[F:37])[CH2:13][C@:14]([C:18]2[CH:19]=[C:20]([NH:25][C:26]([C:28]3[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=3)=[O:27])[CH:21]=[CH:22][C:23]=2[F:24])([CH2:16][F:17])[N:15]=1)(=O)C1C=CC=CC=1.N12CCCN=C1CCCCC2>CO>[NH2:9][C:10]1[O:11][C@H:12]([C:36]([F:37])([F:39])[F:38])[CH2:13][C@:14]([C:18]2[CH:19]=[C:20]([NH:25][C:26]([C:28]3[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=3)=[O:27])[CH:21]=[CH:22][C:23]=2[F:24])([CH2:16][F:17])[N:15]=1

参加物

4

反応物 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732110N-(3-((4S,6S)-2-benzamido-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide

生成物 1

HCID 71668202N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxy-2-pyrazinecarboxamide収率 83%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

A microwave vial was charged with N-(3-((4S,6S)-2-benzamido-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-methoxypyrazine-2-carboxamide (0.11 g, 0.200 mmol, step 1). MeOH (2 ml) was added followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.122 g, 0.801 mmol, Aldrich). The vial was sealed and heated to 75° C. in a microwave (Biotage Initiator) for 1.5 hours. The reaction was cooled to RT and concentrated under reduced pressure. The crude material was purified via silica gel flash chromatography using a gradient of 5-70% EtOAc in hexanes to afford the title compound as a white solid (0.0741 g, 0.166 mmol, 83% yield). MS m/z=446.0 [M+H]+. Calculated for C18H16F5N5O3: 445.343

後処理

  1. customThe vial was sealed
  2. temperatureThe reaction was cooled to RT
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified via silica gel flash chromatography

出典と根拠

ORDレコード
ord-681bbc7f3a9f41c79610cbce4a9b5bf4
出典データセット
uspto-grants-2016_03
特許番号
US09296734B2

反応ノート

読み込み中…