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Cyclopropylamine → N1-cyclopropyl-N4-(5-isoquinolyl)-1,4-cyclohexanediamine

HRID 1352167
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HRID 1352167 반응식
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][CH:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CO>CO>[CH:19]1([NH:22][CH:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)[CH2:13][CH2:14]2)[CH2:21][CH2:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178381944-(5-Isoquinolylamino)-1-cyclohexanone2회HCID 21893726Hydrochloride methanol

생성물 1

HCID 9835432N1-cyclopropyl-N4-(5-isoquinolyl)-1,4-cyclohexanediamine수율 15.7%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

4-(5-Isoquinolylamino)-1-cyclohexanone (intermediate 4) (60 mg) and cyclopropylamine (30 mg) were dissolved in methanol (1 ml), and sodium triacetoxyborohydride (105 mg) was added by portions to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. Hydrochloric acid-methanol was then added thereto, and the reaction mixture was. stirred and was then concentrated. The residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions containing respective compounds, followed by extraction with chloroform-propanol (3/1). The organic layers were dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure to give an anti-form compound (11 mg) and a syn-form compound (12 mg).

후처리

  1. stirringstirred
  2. concentrationwas then concentrated
  3. customThe residue was purified by HPLC [0.5% aqueous trifluoroacetic acid solution/acetonitrile]
  4. additionA saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added to fractions
  5. additioncontaining respective compounds
  6. extractionfollowed by extraction with chloroform-propanol (3/1)
  7. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under the reduced pressure

출처 및 근거

ORD 기록
ord-d40f007530664318aed17527ba5aa410
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07217722B2

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