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Dimethylformamide → 10-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244222
ノート
印刷プレビュー

反応式

HRID 2244222 の反応式
S(Cl)(Cl)=O.[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1)#[N:6].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:30][C:31]([C:33]2[N:42]3[C:36]([CH2:37][NH:38][C:39]4[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=4[CH2:41]3)=[CH:35][CH:34]=2)=[O:32])[CH:24]=1.CN(C)C=O>O1CCOCC1>[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([N:38]2[C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[CH2:41][N:42]3[C:33]([C:31]([NH:30][CH2:29][C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[O:32])=[CH:34][CH:35]=[C:36]3[CH2:37]2)=[O:22])=[CH:18][CH:19]=1)#[N:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22053658N-(3-Pyridinylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideHCID 686894952'-(Cyanomethyl)-1,1'-biphenyl-4-carboxylic acid

生成物 1

HCID 1595170510-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 20 mL of thionyl chloride and 0.243 g (0.001 mol) of 2′-(cyanomethyl)-1,1′-biphenyl-4-carboxylic acid of Step A was heated under reflux for 1 hour. The excess thionyl chloride was removed in vacuo. To the residue was added 35 mL of dry 1,4-dioxane, 0.318 g (0.001 mol) of N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide and 0.122 g (0.001 mol) of N,N-dimethylformamide. The reaction was heated under reflux for three hours, cooled and evaporated to dryness. The residue was collected, washed with water and triturated with ether to give 0.62 g. of a tan solid, m.p. 105-108° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe excess thionyl chloride was removed in vacuo
  4. temperatureThe reaction was heated
  5. temperatureunder reflux for three hours
  6. temperaturecooled
  7. customevaporated to dryness
  8. customThe residue was collected
  9. washwashed with water
  10. customtriturated with ether
  11. customto give 0.62 g

出典と根拠

ORDレコード
ord-ea36873d3d2746f9b0f397cf0441c0dd
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678787B2

反応ノート

読み込み中…

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