Acetic Acid → 7-Butyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester

HRID 10092

반응식

HRID 10092 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:18][CH:17]2[CH2:19][CH:10]([C:11]3[CH:12]=[C:13]([NH2:25])[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][C:16]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26]C(O)=O.C(OC=C(C#N)C#N)C.CO.C(Cl)Cl>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:19][CH:17]([C:16]3[CH:15]=[C:14]4[C:13](=[CH:12][C:11]=32)[N:25]=[CH:26][N:20]4[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 671522-(Ethoxymethylene)propanedinitrileHCID 21226129Dichloromethane methanolHCID 542004584-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester

생성물 1

HCID 542668237-Butyl-5,7,13-triazatetracyclo[9.3.1.02,10.04,8]pentadeca-2(10),3,5,8-tetraene-13-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

4-Butylamino-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester (440 mg, 1.27 mmol) was dissolved in ethanol (20 mL) and HOAc (2 mL) and treated with ethoxymethylenemalononitrile (186 mg, 1.52 mmol). The resulting mixture was warmed to 60° C. and stirred 18 hours. The reaction was cooled, concentrated, treated with H2O and saturated aqueous Na2CO3 solution then extracted with ethyl acetate (3×50 mL) and dried (Na2SO4). After filtration and concentration, the residue was chromatographed to provide a yellow oil. (400 mg, 89%). (TLC 5% methanol/CH2Cl2 (NH3) Rf 0.70).

후처리

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. additiontreated with H2O and saturated aqueous Na2CO3 solution
  4. extractionthen extracted with ethyl acetate (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationAfter filtration and concentration
  7. customthe residue was chromatographed
  8. customto provide a yellow oil

출처 및 근거

ORD 기록
ord-5fd698ef781248f897af3e0a916d0162
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091372B2

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