Methyl chloroformate → HCID 11623951, compound

HRID 1668775Notes

Reaction equation

HRID 1668775 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([CH3:20])[N:11]=2)[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Na+].[Na+].Cl[C:35]([O:37][CH3:38])=[O:36]>C1COCC1.C(OCC)(=O)C.O>[CH3:20][C:12]1[N:11]=[C:10]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:35]([O:37][CH3:38])=[O:36])=[CH:3][CH:4]=2)[CH3:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

8

Reactant 4

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

Product 1

HCID 11623951HCID 11623951, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (4-amino-phenyl)-(2-methyl-quinazolin-4-yl)-methylamine (75 mg, 0.28 mmol) in 5 mL of THF with K2CO3 (80 mg, 0.58 mmol) and Na2SO4 (80 mg, 0.56 mmol) cooled at 0° C. was added methyl chloroformate (200 uL, 2.6 mmol), followed by 500 uL of water dropwise while stirring vigorously. The mixture was stirred for 5 min at 0° C., and diluted with 25 mL of ethyl acetate. The mixture was washed with saturated NaHCO3, the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by column chromatography (45% ethyl acetate/hexane) to give the title compound (65 mg, 0.20 mmol, 71%). 1H NMR (CDCl3): 7.74 (m, 1H), 7.53 (ddd, J=8.4, 6.6, 1.8, 1H), 7.40 (m, 2H), 7.04-7.12 (m, 3H), 6.97 (m, 1H), 6.73 (s, broad, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.73 (s, 3H).

Workup

  1. stirringThe mixture was stirred for 5 min at 0° C.
  2. washThe mixture was washed with saturated NaHCO3
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by column chromatography (45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2838cd12eded4bf7adbcd5de0b8c2392
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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