N-Boc-N-methylethylenediamine → HCID 67269617, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Bromo-3-(6-chloro-2-cyclopentyl-2-H-pyrazolo[3,4-d]pyrimidin-4-yl)-1,3-dihydro-indol-2-one (50 mg, 0.115 mmol) (Example 182), N′-BOC-N′-methylethylenediamine (200 mg, 1.15 mmol) and ethanol (2 mL) were heated to 130° C. in a microwave for 10 minutes. The reaction was concentrated, treated with ethyl ether and filtered to give 36 mg (55%) of the product. The product was dissolved in 4N HCl in dioxane (3 mL) and stirred at rt for 1 hr. The reaction was concentrated, treated with acetone and filtered. The solid was washed with acetone, ethyl ether and pumped dry to give 9 mg (28%) of Example 378. Example 378: 1H NMR (400 MHz, TFA-d) δ 8.9 (s, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4 (d, 1H), 5.1 (m, 1H), 4.3 (m, 2H), 4.0 (m, 4H), 3.1 (m, 3H), 2.1-2.8 (m, 8H); MS (m/e) 470 (M+1); HPLC (99%) purity, retention time 3.040 minutes—Method C; mp 201-204° C.

Provenance & Evidence