Phosphorus oxychloride → HCID 59333340, compound

HRID 1893490Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([NH:13][C:14](=O)[C:15]3[N:16]2[CH:19]=[CH:20][N:21]=3)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:29])=O>>[CH2:1]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[C:14]([Cl:29])[C:15]3[N:16]2[CH:19]=[CH:20][N:21]=3)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 59333331HCID 59333331, compound

Product 1

HCID 59333340HCID 59333340, compoundYield 47%

Procedure

A solution of 8-(benzylamino)-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-4(5H)-one (72 mg; 0.2 mmol; 1 eq) and N,N′-dimethylaniline (0.2 ml) in phosphoryl chloride (2 ml) is stirred at 135° C. under argon for 2 h. Concentration, partition (ice water/ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulfate), concentration and purification by prep CCM on silicagel (dichloromethane/methanol 90:10) affords the title product (35 mg; 0.093 mmol; 47%) as a yellow solid.

Workup

concentrationConcentration
custompartition
extraction(ice water/ethyl acetate), extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
customdrying
concentration(magnesium sulfate), concentration and purification by prep CCM on silicagel (dichloromethane/methanol 90:10)

Sources & evidence

ORD record: ord-0dd840b77b9e455b8a119021b31e8642
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513250B2

Reaction notes

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