Reaction SMILES: [Cl:1]CCCN1C2C(=CC=C([N+]([O-])=O)C=2)C=C1.N1CCCC1.[N:22]1([CH2:28][CH2:29][CH2:30][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([NH:40][C:41]([C:43]4[S:44][CH:45]=[CH:46][CH:47]=4)=[NH:42])[CH:38]=3)[CH:33]=[CH:32]2)[CH2:27][CH2:26]O[CH2:24][CH2:23]1.I.[ClH:49]>CCOCC.CO>[ClH:1].[ClH:49].[N:22]1([CH2:28][CH2:29][CH2:30][N:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([NH:40][C:41]([C:43]4[S:44][CH:45]=[CH:46][CH:47]=4)=[NH:42])[CH:38]=3)[CH:33]=[CH:32]2)[CH2:27][CH2:26][CH2:24][CH2:23]1
Reactant: N=C(Nc1ccc2ccn(CCCN3CCOCC3)c2c1)c1cccs1
Reactant: O=[N+]([O-])c1ccc2ccn(CCCCl)c2c1
Agent: Cl
Agent: I
Solvent: CCOCC
Solvent: C1CCNC1
Solvent: CO
Product: N=C(Nc1ccc2ccn(CCCN3CCCC3)c2c1)c1cccs1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
Procedure described under Example 40. (Yield: 796.6 mg, greater than 100%) Preparation of 1-(3-chloropropyl)-6-nitro-1H-indole (154): Reaction performed as described in Example 40, using pyrrolidine as nucleophile. The product was purified using silica gel column chromatography (2.5-5% 2M ammonia in methanol, 97.5-95% dichloromethane). Yield: 148.1 mg of compound 154 as a dark yellow oil (86.3%). 1H-NMR (CDCl3) δ 8.43 (s, 1H), 8.02-7.98 (dd, J=2.1, 9 Hz, 1H), 7.66-7.63 (d, J=8.7 Hz, 1H), 7.43-7.42 (d, J=3 Hz, 1H), 6.60-6.59 (d, J=3.3 Hz, 1H), 4.36-4.31 (t, J=6.9 Hz, 2H), 2.49 (bs, 4H), 2.41-2.37 (t, J=6.6 Hz, 2H), 2.10-2.01 (quintet, J=6.7 Hz, 2H), 1.85-1.81 (m, 4H) Preparation of N-(1-(3-(pyrrolidin-1-yl)propyl)-1H-indol-6-yl)thiophene-2-carboximidamide dihydrochloride (155): Reaction performed as described in Example 40, compound 150. Following isolation of the HI salt by precipitation (193.5 mg), the salt was dissolved in ethanol. Treated amberlite resin (3.00 g) was added to the solution, and the mixture stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate (30 mL) and filtered. The filtrate was concentrated to afford a yellow oil. The material was absorbed onto silica gel and purified by silica gel column chromatography (5-10% 2M ammonia in methanol, 95-90% dichloromethane). The resulting yellow oil was found to be the desired product, compound 154, by 1H-NMR. The oil was dissolved in anhydrous dichloromethane (5 mL) and transferred to an argon purged reaction vial. The solution was treated with 1M hydrochloric acid in ether (3 mL) and the salt oiled out immediately. The reaction was stirred for 10 minutes and filtered. The vial and the filter were washed with ethyl acetate and the filtrate discarded. The yellow-brown oil which remained in the reaction vial was dissolved in methanol and the solution poured through the filter. The filter was washed with methanol and all organics combined and concentrated to afford a yellow oil. Additional drying under high vacuum afforded a yellow solid, compound 155. Yield: 116 mg of yellow solid. 1H-NMR (DMSO-d6) δ 7.73-7.72 (d, J=3.6 Hz, 1H), 7.60-7.59 (d, J=4.5, 1H), 7.46-7.43 (d, J=8.1 Hz, 1H), 7.21-7.20 (d, J=3 Hz, 1H), 7.11-7.08 (t, J=4.8 Hz, 1H), 6.92 (s, 1H), 6.60-6.57 (dd, J=1.2, 8.4 Hz, 1H), 6.34-6.33 (d, J=3 Hz, 2H), 4.16-4.12 (t, J=6.9 Hz, 2H), 2.46 (s, 4H), 2.36-2.31 (t, J=6.6 Hz, 2H), 1.93-1.83 (quintet, J=6.7 Hz, 2H), 1.67 (s, 4H). MW 353.