Diisopropylethylamine → (S)-tert-butyl 1-(2-(cyclopropylamino)-3-(methylcarbamoyl)phenylamino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

To a solution of 3-amino-2-(cyclopropylamino)-N-methylbenzamide (1.31 g, 6.38 mmol) in DMF (3 mL) was added Boc-L-Ala-OH (1.21 g, 6.38 mmol), 1,1′-dimethyltriethylamine (2.22 mL, 12.8 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tripyrrolidin-1-ylphosphonium hexafluorophosphate(V) (3.99 g, 7.66 mmol) the resulting mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with water, brine and dried over magnesium sulfate. After being concentrated under reduced pressure, the residue was purified by column chromatography on a silica gel column using EtOAc:DCM (1:1) as eluent to give (S)-tert-butyl 1-(2-(cyclopropylamino)-3-(methylcarbamoyl)phenylamino)-1-oxopropan-2-ylcarbamate: 1H NMR (400 MHz, CDCl3) δ 8.56 (br, 1H), 8.14 (d, J=8 Hz, 1H), 7.18 (d, J=8 Hz, 1H), 6.99 (dd, J=8, 8 Hz, 1H), 6.24 (br, 1H), 6.01 (br, 1H), 4.38 (br, 1H), 3.00 (d, J=4 Hz, 3H), 2.58 (br, 1H), 1.60 (s, 3H), 1.48 (s, 9H), 0.64-0.59 (m, 2H), 0.54-0.49 (m, 2H); LC-MS (ESI) m/z 377.2 [M+H]+.

Provenance & Evidence