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

HRID 1737359노트

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HRID 1737359 반응식
[SH2:1].[Cl:2][C:3]1[C:8]2[C:9](=[O:21])[N:10]3[CH2:20][CH2:19][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17]#[N:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1>N1C=CC=CC=1.C(N(CC)CC)C>[Cl:2][C:3]1[C:8]2[C:9](=[O:21])[N:10]3[CH2:20][CH2:19][C@H:11]3[C:12]3[N:13]([CH:14]=[N:15][C:16]=3[C:17](=[S:1])[NH2:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 402Hydrogen SulfideHCID 53905765(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

생성물 1

HCID 86753957(S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-thiocarboxamide수율 35%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8471Triethylamine용매

실험 절차

A stream of hydrogen sulphide was conducted for 1 hr. through a solution of 11.3 g (0.0396 mol) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile in 230 ml of pyridine and 2.3 ml of triethylamine. The green solution was left to stand for 48 hrs., then de-gassed with a stream of nitrogen and subsequently completely freed from the solvents. The residue was partitioned between dichloromethane and water and extracted. The pale yellow product was recrystallized in tetrahydrofuran and subsequently in methanol. There were obtained 4.44 g (35%) of (S)-8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-thiocarboxamide as pale yellow crystals; m.p. 250-253° and [α]D20 =-330.6° (DMF, c=1%).

후처리

  1. waitThe green solution was left
  2. custom, then de-gassed with a stream of nitrogen
  3. customThe residue was partitioned between dichloromethane and water
  4. extractionextracted
  5. customThe pale yellow product was recrystallized in tetrahydrofuran and subsequently in methanol

출처 및 근거

ORD 기록
ord-ad1704dd96c44649acb50b8090db0c8c
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962450

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