Dimethylformamide → N,N-diethylethanamine;methyl butanoate

HRID 323234

反応式

HRID 323234 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 131722484N,N-diethylethanamine;methyl butanoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21980445Ethyl acetate methanol triethylamine溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba28978f1ed94c70867ed611c4592984
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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