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

HRID 1984978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984978
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-cdea657d15d349878d5f68976fbb48a4
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544803B2

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