Methanesulfonyl chloride → HCID 68478043, compound

HRID 2380871Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=[C:9]([NH2:26])[CH:8]=1>N1C=CC=CC=1>[F:6][C:7]1[C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=[C:9]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methanesulfonylchloride (93 μL) was added dropwise to a solution of 5-fluoro-4-(4-fluorophenyl)-2.2-dimethyl-2H-1,3-benzoxazin-7-amine (a compound of Reference Example 2, 87 mg) in pyridine (2 mL), and said mixture was stirred at 40° C. overnight. The reaction mixture was concentrated in vacuo, and the residue was dissolved in chloroform. The solution was washed successively with water, 10% hydrochloric acid and brine, filtered through a column of porous diatomite [Chem Elut (trade name), Varian Inc.], and the filtrate was concentrated in vacuo. The resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=85/15 to 30/70) to give the titled compound (21 mg) as a colorless powder.

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionthe residue was dissolved in chloroform
washThe solution was washed successively with water, 10% hydrochloric acid and brine
filtrationfiltered through a column of porous diatomite [Chem Elut (trade name), Varian Inc.]
concentrationthe filtrate was concentrated in vacuo
customThe resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=85/15 to 30/70)

Sources & evidence

ORD record: ord-c737194ee7cc4ab2a1d0bd5eba1cf76c
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258131B2

Reaction notes

Loading…