Trichloroacetyl chloride → n-{2-[4-(2-Tert-butyl-1,1,3-trioxo-2,3-dihydro-1h-1lambda6-isothiazol-5-yl)-phenyl]-1-cyano-ethyl}-3-trifluoromethyl-benzenesulfonamide

HRID 724606Notes

Reaction equation

[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C@H:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)(=[O:25])=[O:24])[C:19]([NH2:21])=O)=[CH:13][CH:12]=2)[S:6]1(=[O:37])=[O:36])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>C(Cl)Cl.C(OCC)(=O)C>[C:1]([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH:18]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=3)(=[O:25])=[O:24])[C:19]#[N:21])=[CH:15][CH:16]=2)[S:6]1(=[O:36])=[O:37])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.37-B of Step 2 (367 mg, 0.66 mmol) in methylene chloride (7.6 mL) was treated with triethylamine (274 μL, 2.0 mmol) followed by trichloroacetyl chloride (117 μL, 1.1 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h, diluted with ethyl acetate (25 mL), washed with water (2×20 mL) and brine (20 mL), dried with sodium sulfate, filtered, and concentrated to a crude residue which was purified by flash column chromatography to yield the desired product (158 mg, 45%). LCMS found for C23H26F3N4O5S2 (M+NH4)+: m/z=559.

Workup

washwashed with water (2×20 mL) and brine (20 mL)
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated to a crude residue which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-4cebb6e4cc4f4a47a910e2d1f58ddebe
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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