Acetone → HCID 23155961, compound

HRID 1714774Notes

Reaction equation

HRID 1714774 reaction equation
[CH3:1][C:2]([CH3:4])=O.[NH2:5][N:6]1[C:15](=[O:16])[C:14]2[CH2:13][C:12]3([O:20][CH2:19][CH2:18][O:17]3)[CH2:11][CH2:10][C:9]=2[N:8]=[C:7]1[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)[CH2:27][CH2:26]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>O>[CH2:19]1[CH2:18][O:17][C:12]2([CH2:11][CH2:10][C:9]3[N:8]=[C:7]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][N:28]([C:31]5[CH:40]=[CH:39][C:38]6[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=6)[N:32]=5)[CH2:29][CH2:30]4)[N:6]([N:5]=[C:2]([CH3:4])[CH3:1])[C:15](=[O:16])[C:14]=3[CH2:13]2)[O:20]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23155901HCID 23155901, compound

Product 1

HCID 23155961HCID 23155961, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of 29 ml of acetone and 1 ml of water, 229 mg of 3-amino-6,6-ethylenedioxy-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one as synthesized in Example 4-66 and 59 mg of pyridinium p-toluenesulfonate were added and heated under reflux for 112 hours. After cooling, the reaction mixture was extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purifying the residue on silica gel column chromatography (methanol:methylene chloride=1:9) to provide 194 mg (78%) of 6,6-ethylenedioxy-3-isopropylideneamino-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one.

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureunder reflux for 112 hours
  4. temperatureAfter cooling
  5. extractionthe reaction mixture was extracted with methylene chloride
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customPurifying the residue on silica gel column chromatography (methanol:methylene chloride=1:9)

Sources & evidence

ORD record
ord-9ca7afcfa35c4081a7cf46843fa69ec1
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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