Water → 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepine-6-thione

HRID 1046990노트

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HRID 1046990 반응식
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=O)[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.O>N1C=CC=CC=1>[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[S:26])[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 87949Lawesson's reagent

생성물 1

HCID 454962295,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepine-6-thione

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

A mixture of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (3.00 g, 14 mmol) and Lawesson's reagent (6.51 g, 16 mmol) in pyridine (40 mL) was heated to 100° C. for 18 hours. After cooling to room temperature the mixture was poured into water and stirred. The precipitate was collected on a filter paper and dried. The crude product (yellow solid) was carried on to the next step without further purification (96%). 1H NMR (DMSO-d6) 400 MHz δ: 11.99 (s, 1H), 8.37, (s, 1H), 7.98 (dd, J=4.6, 1.7 Hz, 1H), 7.96 (dd, J=8.0, 1.7 Hz, 1H), 7.44 (dd, J=7.7, 1.4 Hz, 1H), 7.35 (td, J=7.7, 1.7 Hz, 1H), 7.06 (dd, J=8.0, 1.2 Hz, 1H), 7.01 (dd, J=8.0, 4.6 Hz, 1H), 6.95 (td, J=8.0, 1.2 Hz, 1H); LC/MS [M+H]: 228.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe precipitate was collected on a filter paper
  3. customdried
  4. customThe crude product (yellow solid) was carried on to the next step without further purification (96%)

출처 및 근거

ORD 기록
ord-448bfb118ec4408182701b8f1450fcf7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569331B2

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