Pyridine → 2-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester

HRID 2235137Notes

Reaction equation

HRID 2235137 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14](=[O:35])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][CH2:30][NH:31]3)=[CH:26][CH:25]=2)=[O:23])=[CH:17][C:16]=1[Cl:34].N1C=CC=CC=1>ClCCl>[CH3:12][O:13][C:14](=[O:35])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][CH2:30][N:31]3[S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)(=[O:10])=[O:9])=[CH:26][CH:25]=2)=[O:23])=[CH:17][C:16]=1[Cl:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 686967962-Chloro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid methyl ester

Product 1

HCID 686978212-Chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluorobenzenesulphonyl chloride (0.027 g, 0.137 mmol, 1.05 equiv.) was added to a mixture of 2-chloro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid methyl ester (0.045 g, 0.130 mmol) and pyridine (0.1 ml) in dichloromethane (2 ml) and the mixture shaken for 16 hours. The solution was washed with saturated sodium hydrogen carbonate (2 ml) and 1M aqueous HCl (2 ml) then dried over magnesium sulphate. The solution was evaporated to afford the crude 2-chloro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid methyl ester, 0.097 g, as a red oil. This material was taken onto the next step without further purification. LC @215 nm; Rt 1.64: 100%, m/z (ES+): 502 (M+H).

Workup

  1. washThe solution was washed with saturated sodium hydrogen carbonate (2 ml) and 1M aqueous HCl (2 ml)
  2. dry with materialthen dried over magnesium sulphate
  3. customThe solution was evaporated

Sources & evidence

ORD record
ord-888af1fc5bfd468f954aad5c9a7e24a8
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

Loading…