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

HRID 1643892Notes

Reaction equation

HRID 1643892 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 eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm). 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-7cb1c3ba9ddf46c0a3ffa8a7104c2fe8
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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