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 1509135Notes

Reaction equation

HRID 1509135 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)carbamateYield 57%

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-6-yl)phenyl)cyclobutyl)carbamate (211 mg, 0.45 mmol) in toluene (15 mL) was added lawesson's reagent (181 mg, 0.45 mmol) under nitrogen. The resulting mixture was heated under reflux for 2 h. After cooled down to room temperature, the mixture was concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 5% MeOH in dichloromethane) to give the title compound as a yellow solid (124 mg, 57%). 1H NMR (500 MHz, CDCl3): 9.47 (1H, br s), 7.30-7.24 (7H, m), 7.18 (1H, s), 7.16-7.14 (2H, m), 5.17 (2H, s), 5.04 (1H, br s), 2.55-2.25 (4H, m), 2.10-2.01 (1H, m), 1.85-1.76 (1H, m), 1.44-1.15 (9H, br).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationthe mixture was concentrated to dryness under reduced pressure
  4. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-98c58a132c074717a2576655f35e80ad
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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