Acetic Anhydride → HCID 11630903, compound

HRID 1668773Notes

Reaction equation

HRID 1668773 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(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[C:28]([NH: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)(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

Product 1

HCID 11630903HCID 11630903, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-amino-phenyl)-(2-methyl-quinazolin-4-yl)-methylamine (28 mg, 0.11 mmol) in 2 mL of dichloromethane with triethylamine (50 uL, 0.36 mmol) cooled at 0° C. was added acetic anhydride (50 uL, 0.53 mmol), followed by a few crystals of 4-dimethylaminopyridine, and the mixture was allowed to warm to room temperature. The reaction mixture was stirred for 0.5 h and 25 mL of ethyl acetate was added. The solution was washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by column chromatography (80% ethyl acetate/hexane) to give the title compound (32.5 mg, 0.11 mmol, 100%). 1H NMR (CDCl3): 7.75 (d, J=8.1, 1H), 7.5-7.57 (m, 3H), 6.94-7.12 (m, 4H), 3.60 (s, 3H), 2.72 (s, 3H), 2.42 (s, 3H).

Workup

  1. washThe solution was washed with saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by column chromatography (80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-789585cc3ca6474f860fc9e2cab75eab
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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