Triethylamine → HCID 10187558, compound

Participants

Reaction Steps

Sulfur trioxide-pyridine complex (11 mg, 0.7 mmol) was added to a solution of quinoline-6-carboxylic acid {(S)-3-methyl-1-[(4S,7R)-7-methyl-3-hydroxy-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (130 mg, 0.235 mmol) in DMSO (2.0 ml) and triethylamine (0.2 ml, 1.4 mmol) was stirred at RT for 1 h. The reaction was incomplete; therefore, additional triethyl amine (0.2 ml, 1.4 mmol) and sulfur trioxide-pyridine complex (11 mg, 0.7 mmol) was added and the reaction was stirred an additional hour. The reaction mixture was diluted with water, then was extracted with EtOAc. Then, the organic layer was was extracted with brine. The combined organics were dried with magnesium sulfate, filtered, concentrated in vacuo, and purified by column chromatography (3% MeOH/CH2Cl2) gave the title compound (100 mg, 77%): 1H NMR:9.0 (sm 1H), 8.70 (s, 1H), 7.90–8.30 (m, 6H), 7.50–7.55 (m, 2H), 7.10 (d, 1H), 7.0 (d, 1H), 5.10–5.15 (m, 1H), 4.70–4.80 (m,2H), 4.35–4.40 (m, 1H), 3.85 (d, 1H), 2.0–2.25 (m, 3H), 1.70–1.80 (m, 2H), 1.60–1.70 (m, 2H), 0.90–1.10 (m, 9H); Electrospray mass spec: M+H+=552.4.

Provenance & Evidence