1,1'-Carbonyldiimidazole → HCID 178423908, compound

HRID 443830Notes

Reaction equation

HRID 443830 reaction equation
[CH3:1][C:2]1[C:11]2[NH:10][C:9]3=[CH:12][C:13]([C:15](O)=[O:16])=[N:14][N:8]3[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)([N:21]1C=CN=C1)=O.FC(F)(F)C1C2C(=O)N3N=C(C(N)=O)C=C3NC=2C=CC=1>CN(C)C=O.CCOCC.C(Cl)Cl>[CH3:1][C:2]1[C:11]2[NH:10][C:9]3=[CH:12][C:13]([C:15]([NH2:21])=[O:16])=[N:14][N:8]3[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 178423909HCID 178423909, compoundHCID 178513503HCID 178513503, compound

Product 1

HCID 178423908HCID 178423908, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4,9-dihydro-5-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxylic acid (4.86 g; 0.02 mole) in dimethylformamide (50 ml) is added 1,1'-carbonyldiimidazole (4.86 g; 0.03 mole). The reaction mixture is heated at 100° C. for 12 min, then cooled and diluted with ether (75 ml) and methylene chloride (25 ml). The tan solid is filtered off and suspended in cold (0° C.) DMF (50 ml). Annydrous ammonia is bubbled through for 10 min and the resulting solution is allowed to stand at room temperature overnight. The dimethylformamide solution is evapoated to dryness under reduced pressure and the residue is washed with methylene chloride and ether and dried. Yield 3.0 g; mp 340°-345° C. (d). By the same procedure, starting with the corresponding 8-trifluoromethyl compound, the product obtained is 4,9-dihydro-8-trifluoromethyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide.

Workup

  1. temperaturecooled
  2. filtrationThe tan solid is filtered off
  3. customsuspended in cold (0° C.) DMF (50 ml)
  4. customAnnydrous ammonia is bubbled through for 10 min
  5. washthe residue is washed with methylene chloride and ether
  6. customdried
  7. customthe product obtained

Sources & evidence

ORD record
ord-fc68dd214d5045e1ae3d0073c0a4d6c4
Source dataset
uspto-grants-1981_04
Patent number
US04261996

Reaction notes

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