HCID 67045062, compound → HCID 59129492, compound

Participants

Reaction Steps

To a stirred solution (R)- N-(1-(3-amino-2-hydroxypropyl)-2-tert-butyl-1H-indol-5-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (0.10 g, 0.20 mmol) in methanol (1 mL) was added 2 drops of triethylamine and methylchloroformyl chloride (0.020 mL, 0.25 mmol). After 30 min, the reaction mixture was filtered and purified using reverse phase HPLC providing (S)-methyl 3-(2-tert-butyl-5-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclo-propanecarboxamido)-1H-indol-1-yl)-2-hydroxypropylcarbamate. The retention time on a three minute run is 1.40 mM. LC/MS (M+1)=544.3. 1 H NMR (400 MHz, CDCl3) δ 7.52 (d, 1H, J=2 Hz), 7.30(dd, 1H, J=2, 8 Hz), 7.28(m, 1H), 7.22(d, 1H, J=8 Hz), 7.14(d, 1H, J=8 Hz), 7.04(br s, 1H), 6.97(dd, 1H, J=2, 8 Hz), 6.24(s, 1H), 5.19(1H, br s), 4.31(dd, 1H, J=6, 15 Hz), 4.28(dd, 1H, J=11, 15 Hz), 4.18(m, 1H), 3.70(s, 3H), 3.40(dd, 1H, J=3, 6 Hz), 3.36(dd, 1H, J=3, 6 Hz), 3.26(m, 1H), 1.74(m, 2H), 1.40(s, 9 H), 1.11(m, 2 H).

Provenance & Evidence