Ethyl Acetate → HCID 11596410, compound

HRID 2069195Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].[F:22][C:23]([F:27])([F:26])[CH2:24][NH2:25].C(OCC)(=O)C>O>[N+:12]([C:11]1[CH:10]=[C:9]2[C:4]([C:5](=[O:21])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:7](=[O:15])[NH:8]2)=[CH:3][C:2]=1[NH:25][CH2:24][C:23]([F:27])([F:26])[F:22])([O-:14])=[O:13]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 200 mg (0.628 mmol) of N-(6-fluoro-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide and 1.08 ml (13.68 mmol) of 2,2,2-trifluoro-ethylamine in a closed vial is heated in a microwave reactor at 140° C. for 20 hours. After cooling, the reaction mixture is distributed between ethyl acetate and water, the organic phase dried and concentrated to yield a precipitate which is filtered off and submitted to purification by medium pressure chromatography on a RP-C18 column (20 μM material) with tetrahydrofuran/water 4:3 as eluent, containing 0.1% TFA. During concentration of the fractions the product precipitates and is collected by filtration, giving 63 mg of a red powder, m.p. 250° C. (decomp.).

Workup

temperatureAfter cooling
customthe organic phase dried
concentrationconcentrated
customto yield a precipitate which
filtrationis filtered off
customsubmitted to purification by medium pressure chromatography on a RP-C18 column (20 μM material) with tetrahydrofuran/water 4:3 as eluent
additioncontaining 0.1% TFA
customDuring concentration of the fractions the product precipitates
filtrationis collected by filtration

Sources & evidence

ORD record: ord-23a8c766aecf4b3ea41d0d905c91b554
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299085B2

Reaction notes

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