Hydrochloric Acid → HCID 178463014, compound

HRID 1456023Notes

Reaction equation

HRID 1456023 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([O:24]C)[CH:10]=3)[CH3:2].[H-].[Na+].C(S)CCC.Cl>CN(C=O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[C:11]([OH:24])[CH:10]=3)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8012ButanethiolHCID 24758Sodium hydrideHCID 70086531HCID 70086531, compound

Product 1

HCID 178463014HCID 178463014, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-7-methoxy-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine (4 g, 0.012 mol) in DMF (70 ml) was treated with 60% NaH (2.4 g, 0.06 mol), followed by butane thiol (5.4 g, 0.06 mol). The reaction mixture was refluxed overnight and then was poured into ice-water. The mixture was acidified with 2N HCl and then was extracted with ethyl acetate (2×500 ml). The aqueous layer was treated with solid NaHCO3 to adjust the pH to about 8, then the mixture was extratced with ethyl acetate (2×500 ml). The ethyl acetate layers were combined, washed with water, filtered and evaporated. The solid residue was recrystallized from ethyl acetate (2×) to afford 1.44 g of 1-ethyl-7-hydroxy-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 252°-254° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionwas extracted with ethyl acetate (2×500 ml)
  3. additionThe aqueous layer was treated with solid NaHCO3
  4. washwashed with water
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue was recrystallized from ethyl acetate (2×)

Sources & evidence

ORD record
ord-210feb9c78b8484d99842147ed097253
Source dataset
uspto-grants-1998_12
Patent number
US05843956

Reaction notes

Loading…