1-Hydroxybenzotriazole → 6-[4-(5-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone

HRID 704631Notes

Reaction equation

HRID 704631 reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.O[N:15]1[C:19]2C=CC=C[C:18]=2[N:17]=N1.Cl.[CH2:25](N=C=NCCCN(C)C)[CH3:26].N1([N:42]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH2:45][CH2:44][C:43]2=[O:52])CCNCC1>CN(C)C=O>[CH3:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([N:17]3[CH2:18][CH2:19][N:15]([C:48]4[CH:47]=[C:46]5[C:51](=[CH:50][CH:49]=4)[NH:42][C:43](=[O:52])[CH2:44][CH2:45]5)[CH2:26][CH2:25]3)=[O:13])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 20621695-Methylimidazo[1,2-a]pyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 200728941-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 200728156-[4-(5-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinoneYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-methylimidazo[1,2-a]pyridine-2-carboxylic acid (704 mg), 1-hydroxybenzotriazole (648 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (917 mg) and N,N-dimethylformamide (25 ml) was stirred for 1 hour at ambient temperature. 1-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone (924 mg) was added thereto, and the mixture was stirred for 10 hours at the same temperature. After the solvent was removed, to the residue were added 5% solution of methanol in chloroform (30 ml) and water (20 ml), and the mixture was adjusted to pH 9 with a saturated aqueous solution of potassium carbonate. The separated organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to a column chromatography on silica gel (80 g) and eluted with 10% solution of methanol in chloroform. The fractions containing the desired compound were collected and concentrated. The residual crystal was recrystallized from methanol-ethyl acetate to give 6-[4-(5-methylimidazo[1,2-a]pyridine-2-carbonyl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone (0.8 g).

Workup

  1. stirringthe mixture was stirred for 10 hours at the same temperature
  2. customAfter the solvent was removed, to the residue
  3. additionwere added 5% solution of methanol in chloroform (30 ml) and water (20 ml)
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with 10% solution of methanol in chloroform
  7. additionThe fractions containing the desired compound
  8. customwere collected
  9. concentrationconcentrated
  10. customThe residual crystal was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-f7bb589a4bd34d828e1801204b3d028c
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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