Oxalyl chloride → Tert-butyl 4-phenyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate

HRID 1673491노트

반응식

HRID 1673491 반응식
C(Cl)(=O)C(Cl)=O.[N:7]1([C:13]2[N:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[NH2:22][C:23]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[C:36]1([C:34]2[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])=[C:23]([NH:22][C:19]([C:16]3[CH:17]=[N:18][C:13]([N:7]4[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]4)=[CH:14][CH:15]=3)=[O:21])[CH:35]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 27947616-(Piperidin-1-yl)pyridine-3-carboxylic acidHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

생성물 1

HCID 67342967Tert-butyl 4-phenyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

1.3 mL of methylene chloride, 1.3 μL of N,N-dimethylformamide and 3.031 mL of oxalyl chloride were sequentially added to 69 mg of 6-(piperidin-1-yl)pyridine-3-carboxylic acid at room temperature, and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 54 mg of tert-butyl 2-amino-4-phenylbenzoate, 3.7 mL of methylene chloride and 6.22 mL of triethylamine and stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1] to obtain tert-butyl 4-phenyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate.

후처리

  1. stirringstirred at room temperature for 2 hours
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]

출처 및 근거

ORD 기록
ord-0474b54a31e74b25b72adef816ef68cf
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999132B2

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