Hydrochloric Acid → {4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

HRID 1715855Notes

Reaction equation

HRID 1715855 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)=[O:4].S(Cl)(Cl)=O.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([O:40][CH3:41])=[C:24]([S:26]([N:29]2[C:38]3[C:33](=[CH:34][CH:35]=[C:36]([NH2:39])[CH:37]=3)[CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])[CH:25]=1.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:10](=[O:12])[NH:39][C:36]2[CH:37]=[C:38]3[C:33]([CH2:32][CH2:31][CH2:30][N:29]3[S:26]([C:24]3[CH:25]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=3[O:40][CH3:41])(=[O:28])=[O:27])=[CH:34][CH:35]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 138161444-(2-Methoxy-2-oxoethyl)benzoic acidHCID 684327061-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine

Product 1

HCID 68434762{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-Methoxycarbonylmethyl-benzoic acid (52.00 mg, 0.27 mmol) was suspended in dichloromethane (2.00 mL) and treated with thionyl chloride (95.57 mg, 0.80 mmol). The mixture was stirred at 50° C. for 18 hours, and the volatiles were evaporated. The residue was redissolved in tetrahydrofuran (2.00 mL) and treated with 1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylamine (94.48 mg, 0.27 mmol) and 4-dimethylaminopyridine (66.76 mg, 0.54 mmol). The mixture was warmed to 75° C. and stirred for 2.5 hours. The mixture was treated with HCl 1 N and the slurry extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (dichloromethane/methanol gradient) to yield {4-[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester as an off-white solid, 134.20 mg (95%), MS (ISP): m/e=529.3 (M+H).

Workup

  1. customthe volatiles were evaporated
  2. dissolutionThe residue was redissolved in tetrahydrofuran (2.00 mL)
  3. temperatureThe mixture was warmed to 75° C.
  4. stirringstirred for 2.5 hours
  5. extractionthe slurry extracted several times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. customevaporated
  8. customThe residue was purified by flash chromatography (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-cfaf4664916749e98f4fb40b6508a1c4
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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