Ammonium Chloride → HCID 69809287, compound

Participants

Reaction Steps

To a stirred solution of (R)-2-(1′-(tert-butoxycarbonyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-5-yl)acetic acid (0.020 g, 0.042 mmol), DIEA (0.023 ml, 0.13 mmol), and HBTU (0.017 g, 0.046 mmol) in 1:1 mixture of DCM/DMF (0.2 mL) was added NH4Cl (0.0067 g, 0.13 mmol). The reaction was stirred at about room temperature overnight. An additional equivalent of DIEA and NH4Cl were added and the reaction stirred at about room temperature overnight. The reaction was diluted with DCM, washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, and concentrated. The crude residue was purified by column chromatography (3-5% MeOH/DCM) to yield (R)-tert-butyl 5-(2-amino-2-oxoethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.012 g, 60%). LCMS (APCI+) m/z 478.3 [M+H]+; Rt=3.05 min.

Provenance & Evidence