Dichloromethane → HCID 54394052, compound

Participants

Reaction Conditions

Reaction Steps

(R)-5-(4-Benzyl-1,3-thiazol-2-yl)-3-(N-benzyloxycarbonylpyrrolidin-2-yl-methyl)-1H-indole was used, and the reaction was heated at 40° C. for 24 hours. Chromatography using methylene chloride:methanol:ammonium hydroxide [9:1:0.1] afforded the title compound (12%) as an amorphous solid: 1H NMR (CDCl3) δ 9.1 (br s, indole NH), 8.17 (d, J=1.4 Hz, 1H), 7.74 (dd, J=1.6 and 8.5 Hz, 1H), 7.35-7.21 (m, 6H), 7.02 (s, 1H), 6.67 (s, 1H), 4.22 (s, 2H), 3.5 (br s, NH), 3.41-3.29 (m, 1H), 3.03-2.73 (m, 4H), 1.94-1.61 (m, 3H), 1.49-1.38 (m, 1H); 13C NMR (CDCl3)δ 169.9, 157.0, 139.2, 137.4, 129.2, 128.5, 127.7, 126.4, 125.5, 123.8, 121.2, 117.3, 114.3, 113.3, 111.7, 59.2, 46.0, 38.1, 31.5, 31.1, 24.9; HRMS calculated for C23H23N3S 374.1615, found 374.1691.

Provenance & Evidence