Hydrochloric Acid → HCID 178463014, compound

HRID 1458739Notes

Reaction equation

HRID 1458739 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) is treated with 60% NaH (2.4 g, 0.06 mol), followed by butane thiol (5.4 g, 0.06 mol). The reaction mixture is refluxed overnight and then is poured into ice water. The mixture is acidified with 2N HCl and then is extracted with ethyl acetate (2×500 ml). The aqueous layer is treated with solid NaHCO3 to adjust the pH to about 8, then the mixture is extracted with ethyl acetate (2×500 ml). The ethyl acetate layers are combined, washed with water, filtered and evaporated. The solid residue is 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 is refluxed overnight
  2. extractionis extracted with ethyl acetate (2×500 ml)
  3. additionThe aqueous layer is treated with solid NaHCO3
  4. extractionthe mixture is extracted with ethyl acetate (2×500 ml)
  5. washwashed with water
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is recrystallized from ethyl acetate (2×)

Sources & evidence

ORD record
ord-6b8b45e35d6d4ec0849ee4030296481c
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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