[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]3[C:24]([CH3:41])=[N:25][C:26]([CH:29]4[CH2:33][CH2:32][N:31](CC5C=CC=CC=5)[CH2:30]4)=[CH:27][CH:28]=3)[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:42])[O:4][N:3]=1.ClC(OC(Cl)C)=O.CO>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:23]3[C:24]([CH3:41])=[N:25][C:26]([CH:29]4[CH2:33][CH2:32][NH:31][CH2:30]4)=[CH:27][CH:28]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:42])[O:4][N:3]=1To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-{2-methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinyl}-N-(2-methylpropyl)benzenesulfonamide (114 mg, 0.194 mmol) in acetonitrile (3 mL) was added 1-chloroethyl chloroformate (0.027 mL, 0.252 mmol) and the reaction mixture was heated at reflux under nitrogen for 2 hours. To this was added methanol (3 mL) and the reaction mixture was refluxed under nitrogen for 1 hour. The solvent was removed in vacuo. The sample was then purified by mass directed autoprep (formic acid buffered) to give the required product as formic acid salt (33 mg). LCMS (2 min, formic) Rt 0.86 min, m/z (ES+) 499 (M+H).
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