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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Triethylamine → 1,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 2383311
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HRID 2383311 반응식
[CH2:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:22])[C:14]([C:18]([NH:20][OH:21])=[NH:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:38]([C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[O:49][CH:50]([CH3:52])[CH3:51])[C:43](Cl)=O)#[N:39]>O1CCOCC1>[CH2:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]1[C:17]2[C:12](=[C:13]([CH3:22])[C:14]([C:18]3[N:19]=[C:43]([C:42]4[CH:46]=[CH:47][C:48]([O:49][CH:50]([CH3:52])[CH3:51])=[C:40]([C:38]#[N:39])[CH:41]=4)[O:21][N:20]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:2][CH2:3][CH3:4]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 575058423-Cyano-4-isopropoxybenzoyl chlorideHCID 178450882HCID 178450882, 화합물

생성물 1

HCID 595910961,1-Dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate수율 11.1%

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매
2회

실험 절차

To a solution of 1,1-dimethylethyl 1-[2-(butyloxy)-2-oxoethyl]-6-[(hydroxyamino)(imino)methyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 19; 264 mg, 0.629 mmol) in dioxane (4 ml) was added triethylamine (0.263 ml, 1.89 mmol) followed by dropwise addition of 3-cyano-4-[(1-methylethyl)oxy]benzoyl chloride (preparation described in WO 2008128951; 169 mg, 0.755 mmol) in dioxane (2 ml). The resulting mixture was stirred at room temperature for 90 min, then heated at 100° C. for 24 h. The mixture was cooled to room temperature and most of the solvent removed in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The layers were separated, and the aqueous layer further extracted with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography, eluting with 5-25% ethyl acetate in cyclohexane, gave the title compound as a pale yellow oil (41 mg).

후처리

  1. temperatureheated at 100° C. for 24 h
  2. temperatureThe mixture was cooled to room temperature and most of the solvent
  3. customremoved in vacuo
  4. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  5. customThe layers were separated
  6. extractionthe aqueous layer further extracted with ethyl acetate
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography
  11. washeluting with 5-25% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-3256da41959e48aca0cd9caeba789ce3
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263620B2

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