N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamide → 2-[4'-[3-(Pyrrolidino)propylamino]phenyl]-8-methylimidazo[1,2-a]pyridine

HRID 1268684

Reaktionsgleichung

Reaktionsgleichung von HRID 1268684
[N:1]1([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]4[CH:27]=3)=[CH:14][CH:13]=2)=O)[CH2:6][CH2:5][CH2:4]C[CH2:2]1>C1(C)C=CC=CC=1>[N:1]1([CH2:7][CH2:8][CH2:9][NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[N:19]=[C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]4[CH:27]=3)=[CH:16][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:2]1

Komponenten

3

Edukt 1

HCID 22015607N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamide

Produkt 1

HCID 220156602-[4'-[3-(Pyrrolidino)propylamino]phenyl]-8-methylimidazo[1,2-a]pyridineAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of the product of Step C (122 mg) and borane-methylsulfide complex (0.5 mL of a 2M solution in toluene) in toluene (3.5 mL) was stirred and heated at reflux for 18 hours. The mixture was cooled to ambient temperature and evaporated. The residue was treated with 1 M HCl (10 mL) and heated to reflux. The aqueous mixture was cooled to ambient temperature and treated with solid sodium hydroxide until the pH of the mixture was 8. The aqueous mixture was extracted three times with dichloromethane (10 mL each). The combined organic layers were dried over sodium sulfate, decanted and evaporated. The residue was purified via silica gel chromatography (methanol/dichloromethane) to yield the title compound (60 mg). 1H-NMR (CD3OD) δ8.16 (d, J=7.0 Hz, 1H), 7.90 (s, 1H), 7.72 (m, 2H), 7.00 (m, 1H), 6.71 (m, 3H), 3.16 (t, J=7.0 Hz, 2H), 2.59 (m, 9H), 1.86 (m, 2H), 1.65 (m, 4H), 1.50 (m, 2H)

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customevaporated
  4. additionThe residue was treated with 1 M HCl (10 mL)
  5. temperatureheated to reflux
  6. temperatureThe aqueous mixture was cooled to ambient temperature
  7. additiontreated with solid sodium hydroxide until the pH of the mixture
  8. extractionThe aqueous mixture was extracted three times with dichloromethane (10 mL each)
  9. dry with materialThe combined organic layers were dried over sodium sulfate
  10. customdecanted
  11. customevaporated
  12. customThe residue was purified via silica gel chromatography (methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a78ab2a6bf644b99996f78ddef0fe6b3
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199117B2

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