Triethylamine → N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-pyrazole-4-carboxamide

HRID 52091

반응식

HRID 52091 반응식
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:19]1[CH:23]=[C:22]([C:24](O)=[O:25])[CH:21]=[N:20]1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O.O>[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][NH:18][C:24]([C:22]3[CH:23]=[N:19][NH:20][CH:21]=3)=[O:25])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 3015937Pyrazole-4-carboxylic acidHCID 146251023-({4-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine

생성물 1

HCID 19962879N-[3-(4-Piperidinomethyl-2-pyridyloxy)propyl]-pyrazole-4-carboxamide수율 87.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 1.0 g of 3-(4-piperidinomethyl-2-pyridyloxy)propylamine and 0.45 g of 4-pyrazolecarboxylic acid dissolved in 15 ml of dimethylformamide was stirred for 5 minutes, whilst ice-cooling, after which 734 mg of diethyl cyanophosphonate and 0.68 ml of triethylamine were added to the resulting mixture. The mixture was then stirred at room temperature for 3 hours, after which it was diluted with water, and the aqueous mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:9 by volume mixture of methanol and chloroform as the eluent, to give 1.2 g (yield 85%) of the title compound as a white powder, melting at 117°-119° C.

후처리

  1. temperaturecooling
  2. stirringThe mixture was then stirred at room temperature for 3 hours
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and chloroform as the eluent

출처 및 근거

ORD 기록
ord-85d42b925841424baebdad4bc27153ca
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

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