Triethylamine → N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]pyrazole-4-carboxamide

HRID 52058

반응식

HRID 52058 반응식
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([O:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][NH2:19])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:20]1[CH:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[N:21]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]/[CH:16]=[CH:17]\[CH2:18][NH:19][C:25]([C:23]3[CH:24]=[N:20][NH:21][CH:22]=3)=[O:26])[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 136724732-Buten-1-amine, 4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-, (Z)-

생성물 1

HCID 44211249N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]pyrazole-4-carboxamide수율 51%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2.39 g of 4-(4-piperidinomethyl-2-pyridyloxy) -cis-2-butenylamine and 1.08 g of 4-pyrazolecarboxylic acid in 40 ml of dry dimethylformamide was stirred for 5 minutes, whilst ice-cooling. 1.89 g of diethyl cyanophosphonate and 1.65 ml of triethylamine were added to the mixture, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was diluted with water and 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, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the 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 1.65 g (yield 51%) of the title compound as a white powder, melting at 121°-123° C.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel
  7. additionby volume mixture of methanol and chloroform as the eluent

출처 및 근거

ORD 기록
ord-33e63b4db34046c6858d778f8790077d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616579

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