Dimethylformamide → N,N-diethylethanamine;methyl butanoate

HRID 323234

반응식

HRID 323234 반응식
[CH3:1][O:2][C:3]1C=[C:5]([CH:39]=[C:40](OC)[C:41]=1OC)[C:6]([N:8]1[CH2:12][CH2:11][C:10](CCN2CCC(NC3NC4C=CC=CC=4N=3)CC2)(C2C=CC(Cl)=C(Cl)C=2)[CH2:9]1)=O.CN(C)C=[O:49].[H-].[Na+].C(OCCCl)C>ClCCl.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:40]([CH2:41][C:3]([O:2][CH3:1])=[O:49])[CH3:39].[CH2:6]([N:8]([CH2:12][CH3:11])[CH2:9][CH3:10])[CH3:5]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 12341Ethane, 1-chloro-2-ethoxy-HCID 24758Sodium hydrideHCID 98743601-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

생성물 1

HCID 131722484N,N-diethylethanamine;methyl butanoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21980445Ethyl acetate methanol triethylamine용매

반응 조건

온도
100 °C

실험 절차

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (0.54 g, 0.82 mmol) and dimethylformamide (15 mL). Add sodium hydride (0.07 g, 60% in oil, 1.8 mmol). After 1 hour, add 2-chloroethyl ethyl ether (1 mL). Heat to 100° C. After 18 hours, cool to ambient temperature and dilute the reaction mixture with dichloromethane. Extract three times with water, dry the organic layer over Na2SO4, filter and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 25/75/1 methanol/ethyl acetate/triethylamine. Collect the product containing fractions, evaporate in vacuo to give a residue, and chromatograph on silica gel eluting with 20/80/0.5 methanol ethyl acetate/triethylamine to give the title compound: Rf=0.23 (silica gel, 30% methanol/ethyl acetate).

후처리

  1. waitAfter 18 hours
  2. temperaturecool to ambient temperature
  3. extractionExtract three times with water
  4. dry with materialdry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. customCollect the product
  9. additioncontaining fractions
  10. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-ba28978f1ed94c70867ed611c4592984
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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