Hydrochloric Acid → 9-(N,N-Dimethylaminomethyl)-2-(2-fluoropenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one monohydrochloride

HRID 849640Notes

Reaction equation

HRID 849640 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[NH:11][C:10](=[O:15])[N:9]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[N:18]=[C:8]3[C:7]=2[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:33]>C(OCC)(=O)C>[ClH:33].[CH3:26][N:2]([CH2:3][CH:5]1[CH2:14][CH2:13][C:12]2[NH:11][C:10](=[O:15])[N:9]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[N:18]=[C:8]3[C:7]=2[CH2:6]1)[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 154342819-(N,N-Dimethylcarbamyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 193675879-(N,N-Dimethylaminomethyl)-2-(2-fluoropenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one monohydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 100 mL of anhydrous tetrahydrofuron was added 9-(N,N-Dimethylcarbamyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one (70 mg). The mixture was refluxed until the solid had completely dissolved. Refluxing was ceased and 100 mg of lithium aluminum hydride was added to the solution. This mixture was allowed to stand for 20 min before being quenched with ethyl acetate. The quenched reaction mixture was filtered through celite and the solvent removed in vacuo to yield an oil. The oil was then dissolved in 5 mL of ethyl acetate and to this ethyl acetate solution was added 1 mL of HCl saturated ethyl acetate. A solid precipitated which was collected and dried to yield 9-(N,N-Dimethylaminomethyl)-2-(2-fluorophenyl)-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazolin-5(6H)-one monohydrochloride (Compound 24), m.p.>325° C.

Workup

  1. temperatureThe mixture was refluxed until the solid
  2. dissolutionhad completely dissolved
  3. temperatureRefluxing
  4. custombefore being quenched with ethyl acetate
  5. customThe quenched reaction mixture
  6. filtrationwas filtered through celite
  7. customthe solvent removed in vacuo
  8. customto yield an oil
  9. customA solid precipitated which
  10. customwas collected
  11. customdried

Sources & evidence

ORD record
ord-8145cb90e148401080f387a854db1ac6
Source dataset
uspto-grants-2000_01
Patent number
US06013799

Reaction notes

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