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 1509152Notes

Reaction equation

HRID 1509152 reaction equation
[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]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67256382HCID 67256382, compound

Product 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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-a4f73eb1caa84497a890aab44a19b194
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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