Dimethylformamide → HCID 23442404, compound

HRID 2119656Notes

Reaction equation

HRID 2119656 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[C:8](=[O:16])[C:7]2[N:17]([CH3:20])[N:18]=[CH:19][C:6]1=2)[CH3:4].ICC[CH2:24][CH2:25][CH2:26][I:27].[CH3:28]N(C)C=O>>[I:27][C:26]1[CH:25]=[CH:24][CH:4]=[C:3]([N:5]2[C:14]3[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=3[C:8](=[O:16])[C:7]3[N:17]([CH3:20])[N:18]=[CH:19][C:6]2=3)[CH:28]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 123541,5-DiiodopentaneHCID 24758Sodium hydride2×HCID 23442433HCID 23442433, compound

Product 1

HCID 23442404HCID 23442404, compoundYield 46%

Procedure

To a suspension of sodium hydride (60-72% in mineral oil, 0.14 g, 3.5 mmol), which was washed with hexane and dried in vacuo, in N,N-dimethylformamide (25 ml) was added a N,N-dimethylformamide solution of 1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 47, step 2, 0.5 g, 2.3 mmol) at 0° C. The mixture was allowed to warm up to room temperature and stirred for 1 h. After 1,5-diiodopentane (1.74 ml, 11.7 mmol) was added at 0° C., the mixture was stood at room temperature for 2 days. Additional sodium hydride (60-72% in mineral oil, 92 mg, 2.3 mmol) was added at room temperature. The mixture was stirred for 6 h, quenched with water and extracted with ethyl acetate (50 ml×2). The organic layer was dried over magnesium sulfate and concentrated. Purification by column chromatography on silica gel eluting with ethyl acetate/hexane (1:1) gave 436 mg (46%) of the title compound as a yellow solid.

Workup

  1. washwas washed with hexane
  2. dry with materialdried in vacuo, in N,N-dimethylformamide (25 ml)
  3. waitthe mixture was stood at room temperature for 2 days
  4. stirringThe mixture was stirred for 6 h
  5. customquenched with water
  6. extractionextracted with ethyl acetate (50 ml×2)
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-dbd1a456b2914c418ac407b0044c0d8a
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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