Thionyl Chloride → HCID 23442445, compound

HRID 2119661Notes

Reaction equation

HRID 2119661 reaction equation
O[CH2:2][CH2:3][N:4]1[C:13]2[CH:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[C:7](=[O:15])[C:6]2[N:16]([CH3:19])[N:17]=[CH:18][C:5]1=2.S(Cl)([Cl:22])=O>O1CCCC1.CN(C)C=O>[Cl:22][CH2:2][CH2:3][N:4]1[C:13]2[CH:12]=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[C:7](=[O:15])[C:6]2[N:16]([CH3:19])[N:17]=[CH:18][C:5]1=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 23442402HCID 23442402, compound

Product 1

HCID 23442445HCID 23442445, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-hydroxyethyl)-1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 62, step 2, 468 mg, 1.82 mmol) in tetrahydrofuran (10 ml) and N,N-dimethylformamide (5 ml) was added dropwise thionyl chloride (0.20 ml, 2.7 mmol). After stirring at room temperature for 2 h, the mixture was concentrated in vacuo, poured into water (100 ml) and extracted with ethyl acetate (100 ml×3). The combined organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1.5 to ethyl acetate only) to give 151 mg (30%) of the title compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionpoured into water (100 ml)
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1.5 to ethyl acetate only)

Sources & evidence

ORD record
ord-e6ef2f8c9c2844a5bfbe51a0480e9105
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

Loading…