Hydrochloric Acid → HCID 59023832, compound

Participants

Reaction Steps

Sodium percarbonate (0.040 g, 0.25 mmol) was added to a mixture of 2-amino-4-(7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (prepared via General Procedure N from the reaction of Example #F.8.1 with 6-amino-4-chloro-3-cyano-pyrrolo[2,3-d]pyrimidine [prepared by chlorination of the 4-oxo derivative (J. Med. Chem., 2001, 44(12), 1993-2003) using POCl3 (Tet., 2004, 60, 943-959), 0.10 g, 0.24 mmol) in 1N KOH (2.4 mL) at ambient temperature. After about 21 hours, the reaction mixture was acidified with 5N HCl and filtered. The resulting solid was purified by preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min, 5-100% CH3CN/50 mM aqueous ammonium acetate over 30 min, hold at 100% CH3CN for 5 minutes, 21 mL/min) to give an impure solid that was triturated with heptane and filtered to give 2-amino-4-(7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (6.9 mg, 7%); RP-HPLC (Table 1, Method e) Rt 1.64 min; m/z (ESI+): 441.0 (M+H)+.

Provenance & Evidence