Triethylamine → HCID 46199081, compound

Participants

Reaction Steps

1,1-Dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine (40.0 mg, 0.200 mmol) and 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (41.2 mg, 0.200 mmol) were dissolved in N,N-dimethylformamide (1 mL) containing triethylamine (84.2 μL, 0.600 mmol) and a magnetic stir bar. O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (84 mg, 0.22 mmol) was added to the mixture and the resulting solution was allowed to stir for 5 minutes at room temperature. The crude product was then purified by preparative HPLC utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoroacetic acid to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]-indol-7-yl)cyclopropanecarboxamide. ESI-MS m/z calc. 388.2, found 389.2 (M+1)+. Retention time of 2.02 minutes. 1 H NMR (400 MHz, DMSO-d6) δ 8.41(s, 1H), 7.59 (d, J=1.8 Hz, 1H), 7.15(d, J=8.6 Hz, 1H), 7.06-7.02(m, 2H), 6.96-6.90(m, 2H), 6.03(s, 2H), 5.98(d, J=0.7 Hz, 1H), 4.06(t, J=6.8 Hz, 2H), 2.35(t, J=6.8 Hz, 2H). 1.42-1.38(m, 2H), 1.34(s, 6H), 1.05-1.01(m, 2H).

Provenance & Evidence