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 457431ノート

反応式

HRID 457431 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a700a2ddcc534d538ab5b5d29c68e30a
出典データセット
uspto-grants-2007_03
特許番号
US07186870B2

反応ノート

読み込み中…