Dimethylformamide → HCID 70041667, compound

HRID 704637Notes

Reaction equation

HRID 704637 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][C:12]([OH:14])=O)[N:10]=[C:4]2[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C=O.[N:32]1([C:38]2[CH:39]=[C:40]3[C:45](=[CH:46][CH:47]=2)[NH:44][C:43](=[O:48])[CH:42]=[CH:41]3)[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CS(C)=O.C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][C:12]([N:35]3[CH2:36][CH2:37][N:32]([C:38]4[CH:39]=[C:40]5[C:45](=[CH:46][CH:47]=4)[NH:44][C:43](=[O:48])[CH:42]=[CH:41]5)[CH2:33][CH2:34]3)=[O:14])[N:10]=[C:4]2[CH:3]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 326092(7-Methylimidazo[1,2-a]pyridin-2-yl)acetic acidHCID 13236366HCID 13236366, compound

Product 1

HCID 70041667HCID 70041667, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 7-methylimidazo[1,2-a]pyridine-2-acetic acid (571 mg), 1,1'-carbonyldiimidazole (535 mg), N,N-dimethylformamide (4.5 ml) and chloroform (7.5 ml) was stirred for 1 hour at ambient temperature. A solution of 6-(1-piperazinyl)-2(1H)-quinolinone (933 mg), triethylamine (607 mg) and dimethylsulfoxide (20 ml) was added thereto and the mixture was stirred for 2 hours at the same temperature. The resulting precipitates were collected, washed with chloroform,.and dissolved in 15% solution of methanol in chloroform (30 ml) and 5% hydrochloric acid (5 ml). 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 (60 g) and eluted with 10% solution of methanol in chloroform. The fractions containing the object compound were combined and concentrated. The residue was pulverized with diethyl ether and dried to give 6 -[4-(7-methylimidazo[1,2-a]pyridin-2-ylacetyl)-1-piperazinyl]-2(lH)-quinolinone (0.45 g).

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. customThe resulting precipitates
  3. customwere collected
  4. washwashed with chloroform
  5. dissolutiondissolved in 15% solution of methanol in chloroform (30 ml) and 5% hydrochloric acid (5 ml)
  6. dry with materialThe separated organic layer was dried over magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with 10% solution of methanol in chloroform
  9. additionThe fractions containing the object compound
  10. concentrationconcentrated
  11. customdried

Sources & evidence

ORD record
ord-571c9f55fcc5410683241767ce63e4ba
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Reaction notes

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