Diphosgene → 1-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione

HRID 601101Notes

Reaction equation

HRID 601101 reaction equation
[CH2:1]([CH:3]([CH2:17][CH3:18])[CH2:4][NH:5][C:6]1[N:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11]C)=[O:9])[CH3:2].[O:19]=C(Cl)OC(Cl)(Cl)Cl>ClCCCl.O1CCOCC1>[CH2:1]([CH:3]([CH2:17][CH3:18])[CH2:4][N:5]1[C:6]2[N:16]=[CH:15][CH:14]=[CH:13][C:7]=2[C:8](=[O:9])[O:10][C:11]1=[O:19])[CH3:2]

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 67064133Ethyl 2-[(2-ethylbutyl)amino]nicotinate

Product 1

HCID 865921011-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dioneYield 36%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 3A (0.664 g, 2.65 mmol) and diphosgene (1.57 g, 7.96 mmol) in 13 mL of 1,2-dichloroethane and 1.3 mL of 1,4 dioxane were reacted at 80° C. for 16 hours. The reaction was concentrated under vacuum and the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (9:1) to provide the title compound (0.235 g, 36%). 1H NMR (300 MHz, CDCl3) δ 0.95 (m, 6H), 1.40 (m, 4H), 1.52 (m, 2H), 4.21 (m, 1H), 7.25 (m, 1H), 8.41 (dd, J=7.72, 1.84 Hz, 1H), 8.70 (dd, J=4.78, 1.84 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-e18bcf40267b4d2b982c52044c39ec8f
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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