Diisopropylethylamine → HCID 22914671, compound

HRID 1377675Notes

Reaction equation

HRID 1377675 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][NH:9][C:8]2=[O:17])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:27][O:28][C:29]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:27][O:28][C:29]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:30]=1[C:31]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][NH:9][C:8]2=[O:17])[CH2:5][CH2:6]1)=[O:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 130510263,4-dihydro-1-(4-piperidinyl)-2(1H)-Quinazolinone

Product 1

HCID 22914671HCID 22914671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-piperidinyl)-3,4-dihydroquinazolin-2(1H)-one (680 mg, 1.40 mmol) from Step 5 in DCM (15 mL) was added DIEA (0.366 mL, 2.1 mmol) followed by 2,4-dimethoxybenzoyl chloride (309 mg, 1.54 mmol). The reaction was stirred for 2 h and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with 5% aqueous citric acid (50 mL) and saturated aqueous NaHCO3 (2×50 mL). The EtOAc layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography eluting first with 95:5 EtOAc:CHCl3 and then with 95:3:2 EtOAc:CHCl3 :MeOH. The title compound was obtained as a white solid (77% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed with 5% aqueous citric acid (50 mL) and saturated aqueous NaHCO3 (2×50 mL)
  4. dry with materialThe EtOAc layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by pressurized silica gel column chromatography
  8. washeluting first with 95:5 EtOAc

Sources & evidence

ORD record
ord-8d06da6c73af407dbb9c70d014b9dcd8
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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