Pyridine → (S)-N-(1-Benzoyl-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamide

HRID 1363111Notes

Reaction equation

HRID 1363111 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].N1C=CC=CC=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:29]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH2:6][C@H:7]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamide

Product 1

HCID 66758168(S)-N-(1-Benzoyl-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1G (62 mg, 0.2 mmol) in CH2Cl2 (1 mL) was added pyridine (0.049 mL, 0.6 mmol), followed by addition of benzoyl chloride (42 mg, 0.3 mmol). The resulting mixture was stirred at RT under argon for 6 h, then loaded on a silica gel cartridge (10 g), eluting with EtOAc (25-50%) in hexane to give the title compound as a white solid (72 mg, 88%). m.p. 174-175° C., HPLC: 99% at 3.01 min (retention time, Phenom. Luna C18, 4.6×50 mm elating with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 ml/min, monitoring at 220 inn). MS (ES): m/z=418 [M+1]+. Chiral HPLC 100% e.e.; retention time=34.8 min; Conditions: OD (4.6×250 mm); Eluted with 40% isopropanol in hexane at 1 mL/min.

Workup

  1. washeluting with EtOAc (25-50%) in hexane

Sources & evidence

ORD record
ord-570c502e212f4238ab057c313b02fe93
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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