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Dimethylformamide → 4-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl ester

HRID 569008
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HRID 569008 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[CH:19]=[CH:20][CH2:21][OH:22])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)=[O:28].C1(N=C=NC2CCCCC2)CCCCC1.CN(C=O)C>CN(C)C1C=CN=CC=1.O.CCOCC>[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:22][CH2:21][CH:20]=[CH:19][CH:18]([O:17][C:16]2[CH:15]=[CH:14][C:13]([O:12][C:7]3[CH:6]=[N:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=3)=[CH:25][CH:24]=2)[CH3:23])=[O:34])=[CH:31][CH:30]=1)=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide2회HCID 5060574-Carbamoylbenzoic acid2회HCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

생성물 1

HCID 569955344-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl ester수율 26%

시약·촉매·용매

3
HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 1.5 g (4.2 mmol) of the pentenol obtained in Example 3 above, 1.04 g (6.3 mmol) of 4-(aminocarbonyl)benzoic acid, 1.30 g (6.3 mmol) of dicyclohexylcarbodiimide (DDC), 0.05 g of 4-(dimethylamino)pyridine and 20 ml of DMF was stirred at room temperature overnight. An additional 0.3 g of DCC and 0.25 g of 4-(aminocarbonyl)benzoic acid were added and the mixture was stirred an additional 20 hours. The mixture was then poured into ether, water added and filtered. The filtrates were separated, and the organic layer washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with a 3:2 hexane:acetone mixture to give 0.55 g of the desired product as a tan, glassy solid, m.p. 144°-148° C. (Compound 29).

후처리

  1. stirringthe mixture was stirred an additional 20 hours
  2. additionadded
  3. filtrationfiltered
  4. customThe filtrates were separated
  5. washthe organic layer washed with saturated aqueous NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was purified by preparative scale HPLC
  9. washeluting with a 3:2 hexane

출처 및 근거

ORD 기록
ord-b14a26c24dee4b8a997fb67fed5e7b8d
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04731108

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