Lawesson's reagent → HCID 87326808, compound

HRID 1509333Notes

Reaction equation

HRID 1509333 reaction equation
[CH3:1][N:2]1[C:7](=O)[CH2:6][O:5][C:4]2[N:9]=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][CH2:26]4)=[CH:21][CH:20]=3)[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:12][C:3]1=2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:46])=CC=1>C1(C)C=CC=CC=1>[C:32]([O:31][C:30](=[O:36])[NH:29][C:25]1([C:22]2[CH:23]=[CH:24][C:19]([C:10]3[C:11]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:12][C:3]4[N:2]([CH3:1])[C:7](=[S:46])[CH2:6][O:5][C:4]=4[N:9]=3)=[CH:20][CH:21]=2)[CH2:28][CH2:27][CH2:26]1)([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 131734400HCID 131734400, compound

Product 1

HCID 87326808HCID 87326808, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tert-butyl (1-(4-(1-methyl-7-phenyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (200 mg, 0.412 mmol) was suspended in toluene (5 ml). Lawesson's reagent (125 mg, 0.309 mmol) was added at room temperature. 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 (1 mL) and treated with diisopropyl ether (7 mL). A yellow solid crushed out. It was filtered and dried until constant weight (200 mg, 96%). LCMS (Method A): RT=7.08 min, M+1=502.

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 (1 mL)
  5. additiontreated with diisopropyl ether (7 mL)
  6. customA yellow solid crushed out
  7. filtrationIt was filtered
  8. customdried until constant weight (200 mg, 96%)

Sources & evidence

ORD record
ord-bacb46319bb648218797a8498ced2680
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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