(Diethylamino)sulfur trifluoride → cis-1-chloro-N-[2-chloro-4-fluoro-5-(7-fluorohexahydro-1,3-dioxoimidazo[1,5-a]pyridin-2(3H)-yl)phenyl]methanesulfonamide

HRID 1107257Notes

Reaction equation

[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:22](=[O:23])[CH:16]3[CH2:17][CH:18](O)[CH2:19][CH2:20][N:15]3[C:14]2=[O:24])[C:10]([F:25])=[CH:9][C:8]=1[Cl:26])(=[O:5])=[O:4].C(N(S(F)(F)[F:33])CC)C>ClCCl>[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:22](=[O:23])[C@@H:16]3[CH2:17][C@@H:18]([F:33])[CH2:19][CH2:20][N:15]3[C:14]2=[O:24])[C:10]([F:25])=[CH:9][C:8]=1[Cl:26])(=[O:5])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the title compound of Example 11, Step A (771 mg, 1-80 mmol) in dichloromethane (10 mL) was added dropwise diethylaminosulfur trifluoride (0.48 mL, 3.60 mmol) at 0° C. The reaction was stirred at 0° C. for 1 hour, quenched with cold water, and extracted with dichloromethane. The combined organic layers were washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The title compound of Step A, a compound of this invention, was isolated by flash chromatography (332 mg) as a foam melting at 60-64° C. 1H NMR (CDCl3) 87.7 (d, 1H), 7.4 (d, 1H), 7.1 (br s, 1H), 5.28 and 5.12 (two br s, 1 H), 4.6 (s, 2H), 1H), 4.2 (dd, 1H), 3.3 (ddd, 1H), 2.65 (m, 1H), 2.2 (m, 1H), 1.9-1.6 (m, 2H).

Workup

customquenched with cold water
extractionextracted with dichloromethane
washThe combined organic layers were washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-413c62e11ed041f899d0fa13b8bc3322
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060432

Reaction notes

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