Trifluoroacetic anhydride → (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

HRID 1378143ノート

反応式

HRID 1378143 の反応式
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.N1C=CC=CC=1>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 54384682(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide

生成物 1

HCID 53905765(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile収率 100%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of 11.9 g (0.0394 mol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2, 1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide in a mixture of 85 ml of dioxan and 6.8 ml of pyridine was treated at 0° with 7.1 ml (0.051 mol) of trifluoroacetic anhydride. The suspension was stirred at 50° for 3 hrs., cooled and poured into ice-cold water. After stirring for 11/2 hr. the suspension was suction filtered. There were obtained 11.2 g (100%) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carbonitrile as white crystals; m.p. 130° (dec.).

後処理

  1. temperature, cooled
  2. additionpoured into ice-cold water
  3. stirringAfter stirring for 11/2 hr
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-2bc8ddf1dae74ee6973c29e4da1e4332
出典データセット
uspto-grants-1997_09
特許番号
US05665718

反応ノート

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