Dipropylamine → HCID 67267138, compound

HRID 598073Notes

Reaction equation

HRID 598073 reaction equation
Cl[C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:14][CH3:15])[N:3]=1.[CH2:16]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:17][CH3:18]>O1CCCC1.O>[CH2:16]([N:19]([CH2:20][CH2:21][CH3:22])[C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:14][CH3:15])[N:3]=1)[CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 8902DipropylamineHCID 672666982-Chloro-5-methoxy-3-methylquinazolin-4(3H)-one

Product 1

HCID 67267138HCID 67267138, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-5-methoxy-3-methylquinazolin-4(3H)-one (75 mg, 0.334 mmol) and dipropylamine (0.137 ml, 1.00 mmol) in tetrahydrofuran (1 ml) was stirred at 80° C. for 60 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting with 50% ethyl acetate/n-hexane to afford 44 mg (45%) of the title compound.

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography
  6. washeluting with 50% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-628ed0411a0e4958b6f195fd11c0cd7c
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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