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Sodium hydride → N-[3-[(1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]-5-(3-cyclopropylprop-2-ynoxy)pyrazine-2-carboxamide

HRID 1526645
ノート
印刷プレビュー

反応式

HRID 1526645 の反応式
[CH:1]1([C:4]#[C:5][CH2:6][OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[NH2:10][C:11]1[O:12][C@H:13]2[C@@H:15]([C@:16]([C:21]3[CH:22]=[C:23]([NH:28][C:29]([C:31]4[CH:36]=[N:35][C:34](Cl)=[CH:33][N:32]=4)=[O:30])[CH:24]=[CH:25][C:26]=3[F:27])([CH:18]([F:20])[F:19])[N:17]=1)[CH2:14]2.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[NH2:10][C:11]1[O:12][C@H:13]2[C@@H:15]([C@:16]([C:21]3[CH:22]=[C:23]([NH:28][C:29]([C:31]4[CH:36]=[N:35][C:34]([O:7][CH2:6][C:5]#[C:4][CH:1]5[CH2:3][CH2:2]5)=[CH:33][N:32]=4)=[O:30])[CH:24]=[CH:25][C:26]=3[F:27])([CH:18]([F:20])[F:19])[N:17]=1)[CH2:14]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27937573-Cyclopropylprop-2-yn-1-olHCID 90412895N-(3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-chloropyrazine-2-carboxamide

生成物 1

HCID 118232927N-[3-[(1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl]-4-fluorophenyl]-5-(3-cyclopropylprop-2-ynoxy)pyrazine-2-carboxamide
収率 57.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3-cyclopropylprop-2-yn-1-ol (205 mg, 2.137 mmol) in DMF (1 mL) was added sodium hydride (60% dispersion in mineral oil; 8.6 mg, 0.214 mmol) at rt. After 15 min N-(3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-chloropyrazine-2-carboxamide (Example 261, 88 mg, 0.214 mmol) was added and the reaction mixture was stirred at 60° C. for 50 min. Water (1.0 mL) and aqueous, saturated NaHCO3 solution (1 mL) were added. The resulting mixture was then extracted with EtOAc (2×10 mL). The combined organic extracts were washed with water and dried over MgSO4. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (0%-20% MeOH/DCM) to give 58 mg of the title compound as an off-white solid. MS m/z=472 [M+H]+

後処理

  1. extractionThe resulting mixture was then extracted with EtOAc (2×10 mL)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel flash column chromatography (0%-20% MeOH/DCM)

出典と根拠

ORDレコード
ord-dbab56de8be24145bdcf2ac3f6a52531
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085576B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート