1-Pyrrolidinepropanamine → 2'-[(3-Pyrrolidin-1-yl-propylamino)-methyl]-biphenyl-4-carboxylic acid quinolin-7-ylamide

HRID 1984978노트

반응식

HRID 1984978 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH:26]=O)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:28]1([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CO.CC(O)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH2:26][NH:36][CH2:35][CH2:34][CH2:33][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 316701-PyrrolidinepropanamineHCID 5049666Sodium triacetoxyborohydrideHCID 111872782'-Formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide

생성물 1

HCID 113287602'-[(3-Pyrrolidin-1-yl-propylamino)-methyl]-biphenyl-4-carboxylic acid quinolin-7-ylamide

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of 2′-formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide, Example 28, (50 mg, 0.14 mmol), 3-pyrrolidin-1-yl-propylamine (54 mg, 0.42 mmol, Aldrich) in DMF (1 mL) and MeOH (1 mL) was added glacial AcOH (1 drop), and the mixture was stirred at 50° C. for 30 min. Sodium triacetoxyborohydride (136 mg, 0.64 mmol) was added in small portions and the reaction mixture was stirred at 50° C. for 30 min. The reaction mixture was cooled to room temperature and concentrated in vacuo. The solid residue was dissolved in EtOAc (60 mL) and washed with 0.5 N NaOH (10 mL). The EtOAc layer was separated, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (gradient, 5 to 10% (2 M NH3 in MeOH) in CH2Cl2) to provide the title compound as light-yellow oil. MS (ESI, pos. ion.) m/z: 465 (M+1).

후처리

  1. stirringthe reaction mixture was stirred at 50° C. for 30 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe solid residue was dissolved in EtOAc (60 mL)
  5. washwashed with 0.5 N NaOH (10 mL)
  6. customThe EtOAc layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe filtrate was evaporated in vacuo
  11. customthe residue was purified by silica gel column chromatography (gradient, 5 to 10% (2 M NH3 in MeOH) in CH2Cl2)

출처 및 근거

ORD 기록
ord-cdea657d15d349878d5f68976fbb48a4
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544803B2

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