Acetic Anhydride → N-[8-[(2,6-Dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-7-yl]acetamide

HRID 1006680Notes

Reaction equation

HRID 1006680 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=[C:4]2[C:3]=1[NH:13][CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22].[C:23](OC(=O)C)(=[O:25])[CH3:24].C(N(CC)CC)C>C(Cl)Cl>[CH3:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[CH2:14][NH:13][C:3]1[C:4]2[N:5]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:6]=[CH:7][C:2]=1[NH:1][C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 226725947-Amino-2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine

Product 1

HCID 22672580N-[8-[(2,6-Dimethylbenzyl)amino]-2,3-dimethylimidazo[1,2-a]pyridin-7-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-amino-2,3-dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine (example 77) (0.16 g, 0.53 mmol) was dissolved in methylene chloride (5 ml) and acetic anhydride (60 mg) was added. The mixture was stirred over night at ambient temperature. A small amount of triethylamine was added and the solvent was removed under reduced pressure. Chromatography first with methylene chloride:methanol, 95:5 and secondly with methylene chloride:ethyl acetate, 50:50 gave after trituration with diethyl ether 87 mg (47%) as white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customChromatography first with methylene chloride:methanol, 95:5 and secondly with methylene chloride:ethyl acetate, 50:50 gave after trituration with diethyl ether 87 mg (47%) as white solid

Sources & evidence

ORD record
ord-e40d720fba9f4ec7bced24f5810123f2
Source dataset
uspto-grants-2004_09
Patent number
US06790960B2

Reaction notes

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