Cyclohexylamine → N1-Cyclohexyl-N4-(1H-5-indazolyl)-1,4-cyclohexanediamine

HRID 1352158

반응식

HRID 1352158 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][CH:11]3[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CO>CO>[CH:18]1([NH:24][CH:14]2[CH2:15][CH2:16][CH:11]([NH:10][C:6]3[CH:5]=[C:4]4[C:9](=[CH:8][CH:7]=3)[NH:1][N:2]=[CH:3]4)[CH2:12][CH2:13]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

6

반응물 4

HCID 7965CyclohexylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178382714-(1H-5-Indazolylamino)-1-cyclohexanone2회HCID 21893726Hydrochloride methanol

생성물 1

HCID 17838201N1-Cyclohexyl-N4-(1H-5-indazolyl)-1,4-cyclohexanediamine수율 28.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4-(1H-5-Indazolylamino)-1-cyclohexanone (intermediate 3) (57 mg) and cyclohexylamine (50 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 antiform compound (22 mg) and a syn-form compound (23 mg).

후처리

  1. stirringthe reaction mixture was stirred
  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-31f02682d6eb468881fb8077b1e3e10f
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217722B2

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