1,1'-Carbonyldiimidazole → HCID 25014510, compound

Participants

Reaction Conditions

Reaction Steps

To the acid (1,4-oxazino[2,3,4-hi]indole-9-carboxylic acid, 6-cyclohexyl-2,3-dihydro-5-phenyl-) (11.4 mg, 31.5 μmol) in a round-bottomed flask at r.t. under N2 was added a solution of 1,1′-carbonyldiimidazole (CDI) (10.2 mg, 62.9 μmol) in THF (1 ml), and the mixture was stirred at 50° C. for 2 hr. After cooling to r.t., the reaction mixture was added a mixture of N,N-dimethylsulfamide (15.6 mg, 126 μmol) and DBU (21.6 mg, 142 μmol) in THF (0.5 ml), and then stirred at 50° C. for 20.5 hr. After cooling to r.t., the volatiles were evaporated and the residue added hydrochloric acid (1.5 ml, 1N). The aqueous mixture was removed by pipet, and the solid residue purified by preparative thin layer chromatography (250 μm×20 cm×20 cm plate) using 5% MeOH/CH2Cl2 as eluent to give the product, which was then further purified by preparative thin layer chromatography (250 μm×20 cm×20 cm plate) using 20% EtOAc/Hexane as eluent to give the sulfamide (1,4-oxazino[2,3,4-hi]indole-9-carboxamide, 6-cyclohexyl-N-[(dimethylamino)sulfonyl]-2,3-dihydro-5-phenyl-). 1H NMR (500 MHz): (CDCl3—CD3OD) δ 7.60-7.44 (d overlapping with m, 7H), 4.76 (t, J=4.8, 2H), 4.19 (t, J=4.8, 2H), 3.03 (s, 6H), 2.80-2.70 (m, 1H), 2.05-1.88 (b m, 2H), 1.88-1.70 (b m, 4H), 1.45-1.25 (b m, 4H); Analytical HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Flow Rate=5 ml/min, Column: Xterra MS C18 S7 3.0×50 mm; LC/MS: (ES+) m/z (M+H)+=468.14, HPLC Rt=1.987 min.

Provenance & Evidence