Dimethylformamide → 3,4-Dihydroquinoline-1-carboxylic acid[6-(2-trifluoromethylbenzenesulfonylamino)-hexyl]amide

HRID 322484Notes

Reaction equation

HRID 322484 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11].CN(C)C=O.C(N(CC)CC)C.[N+](C1C=CC([O:44][C:45]([N:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:50][CH2:49][CH2:48]2)=O)=CC=1)([O-])=O>>[F:21][C:19]([F:22])([F:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2][C:45]([N:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:50][CH2:49][CH2:48]1)=[O:44])(=[O:12])=[O:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 178488194-nitrophenyl 3,4-dihydroquinoline-1(2H)-carboxylateHCID 22719673n-(6-Aminohexyl)-2-trifluoromethylbenzene sulfonamide hydrochloride

Product 1

HCID 227196723,4-Dihydroquinoline-1-carboxylic acid[6-(2-trifluoromethylbenzenesulfonylamino)-hexyl]amideYield 61%

Procedure

To a solution of N-(6-Aminohexyl) -2-trifluoromethylbenzene sulfonamide Hydrochloride( 0.1 g, 0.27 mmol) dimethyl formamide (3 mL) and triethylamine (0.1 g, 1 mmol) was added 3, 4-Dihydro-2H-quinoline-1-carboxylic acid 4-nitrophenyl ester (0.09 g, 0.3 mmol) and the reaction mixture was stirred at room temperature for 4 h. Solvent was evaporated and purification by preparative TLC afford the titled compound as an oil (0.08 g, 61%).

Workup

  1. customSolvent was evaporated
  2. custompurification by preparative TLC

Sources & evidence

ORD record
ord-af5647c0ba424297b1e60868b4bb97b2
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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