4-Chloroaniline → N-(4-Chlorophenyl)-2-(quinolin-4-ylmethylthio)pyridine-3-carboxamide

HRID 599362Notes

Reaction equation

HRID 599362 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][S:12][C:13]2[C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:3][CH:2]=1.[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:19]([C:18]2[C:13]([S:12][CH2:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=[CH:2][CH:3]=3)=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:21])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 670539532-(Quinolin-4-ylmethylthio)pyridine-3-carboxylic acid

Product 1

HCID 11647134N-(4-Chlorophenyl)-2-(quinolin-4-ylmethylthio)pyridine-3-carboxamideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetrauroniumhexafluorophosphate (140 mg, 0.38 mmol) was added to a solution of 2-(quinolin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference Compound No. 7-1.91 mg, 0.31 mmol), 4-chloroaniline (52 mg, 0.40 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.74 mmol) in anhydrous N,N-dimethylformamide (2.0 mL) at room temperature, and the mixture was stirred for 24 hours. Ethyl acetate (50 mL) was added thereto, and the whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL, twice) and brine (50 mL), The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the precipitated solid was filtered off and washed with a mixture of diethyl ether and ethyl acetate (1:1). The resulting solid was dried at 50° C. under reduced pressure to give 93 mg of the target compound as a reddish-brown solid (Yield: 75%)

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL
  2. dry with materialtwice) and brine (50 mL), The organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off
  5. washwashed with a mixture of diethyl ether and ethyl acetate (1:1)
  6. customThe resulting solid was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-3bd7756da98d44058aadb589a1dc0187
Source dataset
uspto-grants-2011_03
Patent number
US07897774B2

Reaction notes

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