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 1509152ノート

反応式

HRID 1509152 の反応式
[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]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 67256382HCID 67256382、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-a4f73eb1caa84497a890aab44a19b194
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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