Phosphorus oxychloride → HCID 90409257, compound

HRID 589136Notes

Reaction equation

P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:11]([C:12]2[C:21]3[O:20][CH2:19][CH:18]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[N:17]4[C:28](=O)[NH:29][C:15]([C:16]=34)=[C:14]([F:31])[CH:13]=2)=[C:10]([CH3:32])[O:9][N:8]=1>>[Cl:3][C:28]1[N:17]2[CH:18]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:19][O:20][C:21]3=[C:16]2[C:15](=[C:14]([F:31])[CH:13]=[C:12]3[C:11]2[C:7]([CH3:6])=[N:8][O:9][C:10]=2[CH3:32])[N:29]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 90409066HCID 90409066, compound

Product 1

HCID 90409257HCID 90409257, compound

Conditions

Temperature: 90 °C

Procedure

Phosphoryl chloride (1.5 mL, 16 mmol) was added to a vial charged with 7-(3,5-dimethylisoxazol-4-yl)-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one (32 mg, 0.087 mmol) and the mixture was stirred overnight at 90° C. The mixture was quenched with ice-cold water, diluted with NaHCO3 and extracted with ethyl acetate. The organic extracts were collected and evaporated to afford the title compound. LCMS calc. for C19H15ClFN4O2 (M+H)+: m/z=385.1. found: 385.1.

Workup

customThe mixture was quenched with ice-cold water
additiondiluted with NaHCO3
extractionextracted with ethyl acetate
customThe organic extracts were collected
customevaporated

Sources & evidence

ORD record: ord-44bf340e72244fa7af437cec2ebcba45
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227985B2

Reaction notes

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