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

HRID 8374

Reaction equation

HRID 8374 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N:27]1([CH2:33][CH2:34][C:35](O)=[O:36])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1>ClCCl.CN(C)C=O>[N:27]1([CH2:33][CH2:34][C:35]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[C:10]4[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]4[CH:17]=3)=[CH:6][CH:7]=2)=[O:36])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 1177821-Piperidinepropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27710774-{8-Methylimidazo[1,2-a]pyridin-2-yl}anilineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 22015607N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamideYield 23.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Step B (330 mg) and N,N-diisopropylethylamine (0.28 mL) in dichloromethane (3 mL) and N,N-dimethylformamide (1 mL), was added 1-piperidinepropionic acid (256 mg), WSC.HCl (1-Ethyl-3-(3′dimethylaminopropyl)-carbodiimide.HCl) (312 mg), and 1-hydroxybenzotriazole hydrate (220 mg). The solution was stirred at ambient temperature for approximately 18 hours. The mixture was poured into a separatory funnel and washed sequentially with an equal volume of 1 N sodium hydroxide and water. The organic phase was dried over sodium sulfate, decanted and evaporated. The residue was purified via silica gel chromatography (methanol/dichloromethane) to yield the title compound (128 mg).

Workup

  1. additionThe mixture was poured into a separatory funnel
  2. washwashed sequentially with an equal volume of 1 N sodium hydroxide and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customdecanted
  5. customevaporated
  6. customThe residue was purified via silica gel chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-e9297e9f797943d9b05989f796ddd673
Source dataset
uspto-grants-2006_08
Patent number
US07087757B2

Linked notes

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