Lawesson's reagent → Tert-butyl (1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

HRID 1509152노트

반응식

HRID 1509152 반응식
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=O)[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=[S:45])[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 67256382HCID 67256382, 화합물

생성물 1

HCID 86683631Tert-butyl (1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6yl)phenyl)cyclobutyl)carbamate (5 g, 10.60 mmol) in toluene (380 ml) was added Lawesson's reagent (4.29 g, 10.60 mmol). The resulting mixture was heated under reflux for 5 hours. After it was cooled down to room temperature, the mixture was concentrated to dryness under reduced pressure. The resulting residue was dissolved in the minimum amount of dichloromethane (500 ml) and treated with diisopropyl ether (800 ml). A yellow solid crushed out. It was filtered and dried until constant weight (4.7 g, 91%). LCMS (Method D): RT=1.526 min, M+1=488.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationthe mixture was concentrated to dryness under reduced pressure
  4. dissolutionThe resulting residue was dissolved in the minimum amount of dichloromethane (500 ml)
  5. additiontreated with diisopropyl ether (800 ml)
  6. customA yellow solid crushed out
  7. filtrationIt was filtered
  8. customdried until constant weight (4.7 g, 91%)

출처 및 근거

ORD 기록
ord-a4f73eb1caa84497a890aab44a19b194
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221838B2

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