Acetic Anhydride → 3-methyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one

HRID 1714785Notes

Reaction equation

HRID 1714785 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH:23][C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[C:30](O)=[O:31])=O)[CH2:13][CH2:12]1.C(OC(=O)C)(=O)C.[CH3:40][NH2:41].CO>O1CCCC1>[CH3:40][N:41]1[C:30](=[O:31])[C:25]2[CH2:26][CH2:27][CH2:28][CH2:29][C:24]=2[N:23]=[C:21]1[CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 231556192-[5-(4-Quinolin-2-ylpiperazin-1-yl)pentanoylamino]cyclohex-1-enecarboxylic acidHCID 57454252Monomethylamine methanol

Product 1

HCID 117747983-methyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 ml of tetrahydrofuran, 10.0 g of 2-[5-(4-quinolin-2-ylpiperazin-1-yl)-pentanoylamino]cyclohex-1-enecarboxylic acid as synthesized in above Step 7-1-E was suspended, and to the suspension, 7.0 g of 3 equivalent of acetic anhydride was added, followed by an hour's heating under reflux. The solution was cooled with ice, and while continuing the cooling, 35.6 ml of excessive 40% methylamine-methanol solution was gradually added. After about 10 minutes' refluxing under stirring, the temperature was cooled to room temperature and the solution was concentrated under reduced pressure. After addition of 80 ml of distilled water and 30 minutes' stirring, precipitated crystals were recovered by filtration and dried to provide 8.83 g (89.3%) of 3-methyl-2-[4-(4-quinolin-2-ylpiperazin-1-yl)butyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one.

Workup

  1. waitfollowed by an hour
  2. temperature's heating
  3. temperatureunder reflux
  4. temperatureThe solution was cooled with ice
  5. additionwas gradually added
  6. temperatureAfter about 10 minutes' refluxing
  7. concentrationthe solution was concentrated under reduced pressure
  8. additionAfter addition of 80 ml of distilled water and 30 minutes'
  9. stirringstirring
  10. customprecipitated crystals
  11. filtrationwere recovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-7bd7bf33637b4ac5804edae5039618bf
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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