3-Bromopropionitrile → HCID 178447836, compound

Participants

Reaction Steps

In a 10 mL glass microwave reaction vessel under nitrogen, 17 mg (0.425 mmol) sodium hydride (obtained as a 60% dispersion in mineral oil) was slurried with a solution of 0.133 g (0.28 mmol) N-Boc-N′-{2-[2-phenyl-5-(4-propyl-cyclohexyl)-pyrrol-1-yl]-acetyl}-guanidine from Step 8 in 4 ml anhydrous DMF, and 41 mg (0.28 mmol) 3-bromopropionitrile. The reaction vessel was capped and microwave at 150° C. for 460 sec in a microwave reactor. (Emrys™ Microwave Synthesizer, Personal Chemistry Inc., Foxboro, Mass.) The reaction was concentrated and redissolved in 2 mL CH2Cl2. 0.66 mL trifluoroacetic acid was added and the reactions were shaken for 1 hr. The reactions were then concentrated, redissolved in DMSO:MeCN (4:1) and purified by Gilson preparative 4HPLC to afford 34.5 mg of the title compound [2LC-MS data; molecular ion and retention time): m/z 434 (M+H); 2.77 min] as an oil.

Provenance & Evidence