Hydrochloric Acid → HCID 178464050, compound

HRID 2073780Notes

Reaction equation

HRID 2073780 reaction equation
C(S)CCC.[CH2:6]([N:8]([CH2:27][CH3:28])[CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]3[C:22]([CH:23]=[C:14]2[C:13]([NH2:26])=[N:12]1)=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[CH:18]=3)[CH3:7].[H-].[Na+].Cl.CN(C)C=[O:35]>>[NH2:26][C:13]1[NH:12][N:11]([CH2:10][CH2:9][N:8]([CH2:6][CH3:7])[CH2:27][CH3:28])[C:15]2[C:14]=1[CH:23]=[C:22]1[C:17](=[CH:18][C:19]([O:24][CH3:25])([OH:35])[CH:20]=[CH:21]1)[N:16]=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8012ButanethiolHCID 24758Sodium hydrideHCID 14822487HCID 14822487, compound

Product 1

HCID 178464050HCID 178464050, compound

Procedure

Butanethiol (5.34 ml) was added to a mixture of 13.0 g 1-[2-(diethylamino)ethyl]-7-methoxy-1H-pyrazolo[3,4-b]quinolin-3-amine (Example 22) and 2.0 g sodium hydride in 150 ml dimethylformamide, and the reaction mixture was heated at reflux for about 16 hours. The resulting mixture was treated with 2N hydrochloric acid to pH 7-8, the volatile materials removed by distillation and evaporation, and the residue acidified with 2N hydrochloric acid and extracted with ethyl acetate. The aqueous layer was made strongly basic, extracted to remove starting material, and finally adjusted to PH 8 to obtain the desired product. There was obtained 2.5 g of 3-amino-1-[2-(diethylamino)ethyl]-7-methoxy-1H-pyrazolo[3,4-b]quinolin-7-ol, orange solid, m.p. 232°-235° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for about 16 hours
  3. customthe volatile materials removed by distillation and evaporation
  4. extractionextracted with ethyl acetate
  5. extractionextracted
  6. customto remove

Sources & evidence

ORD record
ord-5a4b64aa9116420d97b5dba466bc51cb
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Reaction notes

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