Pyridine → HCID 76568002, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][CH:11]([C:16]([CH3:18])=[CH2:17])[C:10]21[C:26]1[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=1)[NH:20][C:19]2=[O:28].[CH3:29][S:30](Cl)(=[O:32])=[O:31].N1C=CC=CC=1>C(#N)C>[Cl:27][C:23]1[CH:22]=[C:21]2[NH:20][C:19](=[O:28])[C:10]3([CH:9]([C:3]4[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=4[NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:14][C:13](=[O:15])[NH:12][CH:11]3[C:16]([CH3:18])=[CH2:17])[C:26]2=[CH:25][CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of racemic (2′R,3R,4′S)-4′-(2-amino-5-chloro-phenyl)-6-chloro-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.1 mmol), methanesulfonyl chloride (0.0092 mL, 0.15 mmol), in acetonitrile (5 mL) was added pyridine (23 mg, 0.3 mmol) at r.t. The reaction mixture was stirred for 4 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated. The residue was purified with Prep. HPLC to give the title compound as a white solid (Yield: 8 mg).