Succinic anhydride → 4-(2-(((8-(2-Ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)carbonyl)amino)ethoxy)-4-oxobutanoic acid

HRID 427477Notes

Reaction equation

HRID 427477 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([NH:23][CH2:24][CH2:25][OH:26])=[O:22])=[CH:6][N:5]2[C:27]=1[CH3:28].[C:29]1(=[O:35])[O:34][C:32](=[O:33])[CH2:31][CH2:30]1>CC(C)=O>[CH2:19]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:27]([CH3:28])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[C:7]([C:21]([NH:23][CH2:24][CH2:25][O:26][C:29](=[O:35])[CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:22])[CH:8]=1)[CH3:20]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 98212412,3 dimethyl-8-(2-ethyl-6-methylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 99568284-(2-(((8-(2-Ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridin-6-yl)carbonyl)amino)ethoxy)-4-oxobutanoic acidYield 227.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3 dimethyl-8-(2-ethyl-6-methylbenzylamino)-N-hydroxyethyl-imidazo[1,2-a]pyridine-6-carboxamide (250 mg, 0.263 mmol) and succinic anhydride (100 mg, 1.00 mmol) were added to 7 ml of acetone. The mixture was refluxed for 48 h. The presiptated product was filtered off and washed with acetone and ether to give 288 mg (91%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 48 h
  2. filtrationThe presiptated product was filtered off
  3. washwashed with acetone and ether

Sources & evidence

ORD record
ord-c49061fc08704fe09f59989ea9789a07
Source dataset
uspto-grants-2001_11
Patent number
US06313136B1

Reaction notes

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