Hydrochloric Acid → (2-Fluoromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine

HRID 1876098Notes

Reaction equation

HRID 1876098 reaction equation
[F:1][CH2:2][C:3]1[NH:12][C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.COC(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].F[CH2:26]C#N.Cl.[O:30]1CCOC[CH2:31]1>>[F:1][CH2:2][C:3]1[N:12]=[C:11]([N:23]([C:18]2[CH:17]=[CH:22][C:21]([O:30][CH3:31])=[CH:20][CH:19]=2)[CH3:26])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8635Methyl AnthranilateHCID 10420Acetonitrile, fluoro-HCID 312751,4-DioxaneHCID 1362452332-(Fluoromethyl)quinazolin-4(1H)-one

Product 1

HCID 11208709(2-Fluoromethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amineYield 39%

Conditions

Temperature
80 °C

Procedure

2-Fluoromethyl-quinazolin-4(3H)-one: To a solution of 2-amino-benzoic acid methyl ester (151 mg, 1 mmol) and fluoro-acetonitrile (0.14 ml, 2.5 mmol) in dioxane (5 ml) at room temperature was added concentrated HCl (0.05 ml) dropwise. The mixture was heated at 80° C. for 24 h and then cooled to room temperature. The resulting solid was collected and dissolved in water (10 ml), and the solution was neutralized with saturated aqueous NaHCO3 to pH 7. The solution was extracted by ethyl acetate. The extracts were evaporated, and the residue was purified by column chromatography on silica gel with ethyl acetate and hexane (1:1) as eluent, yielding 70 mg (39%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting solid was collected
  3. dissolutiondissolved in water (10 ml)
  4. extractionThe solution was extracted by ethyl acetate
  5. customThe extracts were evaporated
  6. customthe residue was purified by column chromatography on silica gel with ethyl acetate and hexane (1:1) as eluent

Sources & evidence

ORD record
ord-fc4a540bc49b4727ae3b142f958ff3c9
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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