5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 68695652, compound

HRID 2235160Notes

Reaction equation

HRID 2235160 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][NH:21]3)=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)[CH3:2].[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([O:36][CH3:37])=[C:30]([S:32](Cl)(=[O:34])=[O:33])[CH:31]=1>ClCCl.N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][N:21]3[S:32]([C:30]3[CH:31]=[C:26]([Cl:25])[CH:27]=[CH:28][C:29]=3[O:36][CH3:37])(=[O:33])=[O:34])=[CH:16][CH:15]=2)=[O:13])=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 68694214HCID 68694214, compound

Product 1

HCID 68695652HCID 68695652, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid ethyl ester (140 mg, 0.43 mmol) in dichloromethane (5 ml) and pyridine (0.15 ml) was treated with 5-chloro-2-methoxy-benzenesulfonyl chloride (159 mg, 0.66 mmol, 1.5 equiv.) and stirred at room temperature for 17 hours. The solvent was then evaporated and the residue purified by flash chromatography (dichloromethane/ether 9:1) to yield 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid ethyl ester as a white foam, 227 mg (100%). MS (ISP): m/e=527.2 (M−H); δH (300 MHz; d6-DMSO) 10.5 (1H, s), 8.02 (1H, d), 7.96 (2H, d), 7.93 (2H, d), 7.85 (1H, d), 7.72 (1H, dd), 7.67 (1H, dd), 7.30 (1H, d), 7.23 (1H, d), 4.30 (2H, q), 3.78 (2H, m), 2.75 (2H, t), 1.74 (2H, m), 1.32 (3H, t).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by flash chromatography (dichloromethane/ether 9:1)

Sources & evidence

ORD record
ord-7ffeb06c6b324f708ff61df0b7dc8cba
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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