Lawesson's reagent → HCID 58458930, compound

HRID 390344Notes

Reaction equation

HRID 390344 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:24][CH2:25][C:26](=O)[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]1[S:45][C:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH:25][N:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58458928HCID 58458928, compound

Product 1

HCID 58458930HCID 58458930, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(benzyloxy)-N-(3-(4-fluorophenyl)-2-oxopropyl)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxamide: (0.12 g, 0.25 mmol) and Lawesson's reagent (0.11 g, 0.275 mmol) in toluene (10 mL) was stirred 15 min at room temperature, 30 min at 60° C. and 2 h at 100° C. The mixture was cooled, concentrated and purified by preparative HPLC on a C18 column using water/MeOH containing 0.1% TFA as eluent to afford the title compound (0.05 g, 43% yield) as a yellow solid. 1HNMR (500 MHz, CDCl3) δ: 7.78 (1H, s), 7.54-7.51 (2H, m), 7.32-7.29 (3H, m), 7.19 (2H, dd, J=8.6, 5.2 Hz), 7.01 (2H, t, J=8.6 Hz), 5.35 (2H, s), 4.15 (2H, s), 4.06-4.00 (4H, m), 1.66 (6H, s). HRMS (M+H) calcd for C26H25N3O3FS: 478.1601. found: 478.1623.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified by preparative HPLC on a C18 column

Sources & evidence

ORD record
ord-f612c235e47c447a91ffcb7a74687fdf
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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