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

HRID 599362
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HRID 599362 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-3bd7756da98d44058aadb589a1dc0187
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07897774B2

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