Triphenylphosphine → N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-piperidinoethyl)-5-isoquinolinesulfonamide

HRID 5745

반응식

HRID 5745 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH3:10])=[CH:4][CH:3]=1.[N:29]1([CH2:35][CH2:36]O)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][N:9]([CH2:11][CH2:12][N:13]([CH2:36][CH2:35][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[S:14]([C:17]2[C:18]3[CH:19]=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:15])=[O:16])[CH3:10])=[CH:27][CH:28]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53675817N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-5-isoquinolinesulfonamide

생성물 1

HCID 53869192N-[2-(4-Chloro-N-methylcinnamylamino)ethyl]-N-(2-piperidinoethyl)-5-isoquinolinesulfonamide수율 74.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 0.39 g of the amorphous compound obtained in Example 190, 0.145 g of 1-piperidinethanol and 0.369 g of triphenylphosphine in 5 ml of tetrahydrofuran, was added dropwise a solution of 0.245 g of diethyl azodicarboxylate in 2 ml of tetrahydrofuran with stirring under ice cooling. The mixture was stirred for 2 hours and evaporated to remove the solvent under a reduced pressure, and resulting residue dissolved in 30 ml of ethyl acetate and extracted three times with 10 ml of 1N hydrochloric acid. The aqueous layer was alkallized with sodium bicarbonate and extracted three times with 10 ml of ehtyl acetate, and the organic extract was dried over magnesium sulfate and evaporated to remove the solvent at a reduced pressure. The resulting residue was applied to a silica gel column and eluted with 2% methanol in chloroform, to obtain 0.37 g of the title compound as a colorless oil.

후처리

  1. stirringThe mixture was stirred for 2 hours
  2. customevaporated
  3. customto remove the solvent under a reduced pressure
  4. customresulting residue
  5. extractionextracted three times with 10 ml of 1N hydrochloric acid
  6. extractionextracted three times with 10 ml of ehtyl acetate
  7. extractionthe organic extract
  8. dry with materialwas dried over magnesium sulfate
  9. customevaporated
  10. customto remove the solvent at a reduced pressure
  11. washeluted with 2% methanol in chloroform

출처 및 근거

ORD 기록
ord-bb0f112c30d04259bcbd03fbf9a0c4bf
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245034

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