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 8375

Reaction equation

HRID 8375 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 220156602-[4'-[3-(Pyrrolidino)propylamino]phenyl]-8-methylimidazo[1,2-a]pyridineYield 53.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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 1M 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) δ 8.16 (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).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customevaporated
  4. additionThe residue was treated with 1M 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)

Sources & evidence

ORD record
ord-e96def60df7d43e5a370fd4e9b82ffa2
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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