[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[N:6][C:7]1[CH:8]=[C:9]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].CS(N1C2C(=CC=C(N)C=2)[CH:26]=[CH:25]1)(=O)=O.[ClH:34].CCOCC>CO.C(O)(C)C>[ClH:34].[CH3:17][S:14]([N:13]1[C:9]2[C:10](=[CH:11][CH:12]=[C:7]([N:6]=[C:2]3[NH:3][CH2:4][CH2:5][NH:1]3)[CH:8]=2)[CH:26]=[CH:25]1)(=[O:16])=[O:15]3.82 g of 2-chloroimidazoline hydrogen sulfate (see Example 6A) was treated with 50 ml of 1M NaOH solution and immediately extracted with CH2Cl2 (3×20 ml). The extracts were dried (K2CO3) and the solution decanted. 10 ml of isopropanol was added and the CH2Cl2 was removed at reduced pressure. The resultant isopropanol solution was added to a refluxing solution of the N-methanesulfonyl-6-aminoindole (2.02 g, 9.61 mmol) in isopropanol (10 mmol). The mixture was refluxed for 3 hr, cooled, and concentrated under vacuum. A portion (800 mg) of the crude product was dissolved in MeOH:H2O (5:1) then 10 g of silica gel was added. The mixture was dried under vacuum and the resulting powder was applied to a silica gel column and eluted with ethyl acetate:MeOH:iPrNH2 (93:5:2) (iPr=isopropyl). The white solid obtained was suspended in MeOH (4 ml) and treated with 3 ml of 1.0M HCl/ether. The solid dissolved then a precipitate formed which was filtered off after chilling the mixture in an ice bath. 590 mg of N-methanesulfonyl-6-(imidazolidin-2-ylideneamino)indole hydrochloride were obtained (mp 167.6-170.6° C.).
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