HCID 178513504, compound → HCID 178513502, compound

HRID 443828Notes

Reaction equation

HRID 443828 reaction equation
O=C1C2C=CC=CC=2NC2=CC(C(O)=O)=NN12.F[C:19]1[CH:28]=[CH:27][C:26]2[NH:25][C:24]3=[CH:29][C:30]([C:32]([NH2:34])=[O:33])=[N:31][N:23]3[C:22](=[O:35])[C:21]=2[CH:20]=1>N1C=CC=CC=1.S(Cl)(Cl)=O>[O:35]=[C:22]1[C:21]2[CH:20]=[CH:19][CH:28]=[CH:27][C:26]=2[NH:25][C:24]2=[CH:29][C:30]([C:32]([NH2:34])=[O:33])=[N:31][N:23]12

Participants

5

Reactant 2

HCID 178513504HCID 178513504, compoundHCID 178524062HCID 178524062, compound

Product 1

HCID 178513502HCID 178513502, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 4,9-dihydro-9-oxo-pyrazolo[5,1-b]-quinazoline-2-carboxylic acid (5 g; 0.022 mole), thionyl chloride (250 ml) and four drops of pyridine is stirred at room temperature for 24 hrs. The reaction mixture is evaporated to dryness under reduced pressure in a water bath at 30°-40° C. The residue is treated with cold (0° C.) concentrated ammonium hydroxide solution (200 ml) and allowed to come to room temperature. The product is filtered off, washed with ether and used in the next step without further purification. Yield 3.2 g; mp 315°-325° C. An analytical sample, recrystallized from dimethylformamide, melts at 335°-340° C. By the same procedure, starting with the corresponding 7-fluoro compound, the product obtained is 4,9-dihydro-7-fluoro-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide.

Workup

  1. customThe reaction mixture is evaporated to dryness under reduced pressure in a water bath at 30°-40° C
  2. additionThe residue is treated with cold (0° C.) concentrated ammonium hydroxide solution (200 ml)
  3. customto come to room temperature
  4. filtrationThe product is filtered off
  5. washwashed with ether
  6. customused in the next step without further purification
  7. customAn analytical sample, recrystallized from dimethylformamide, melts at 335°-340° C
  8. customthe product obtained

Sources & evidence

ORD record
ord-2d0d3e7f568a4483a1c31019a7c68c7a
Source dataset
uspto-grants-1981_04
Patent number
US04261996

Reaction notes

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