Sodium Acetate → 4'-[[(2,6-Dichloro-4-quinazolinyl)amino]methyl][1,1'-biphenyl]-2-carboxylic acid

HRID 2082016Notes

Reaction equation

HRID 2082016 reaction equation
C([O-])(=O)C.[Na+].[Cl:6][C:7]1[N:16]=[C:15](Cl)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:18])[CH:13]=2)[N:8]=1.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1>C1COCC1>[Cl:6][C:7]1[N:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][CH:22]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:18])[CH:13]=2)[N:8]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 104215102,4,6-TrichloroquinazolineHCID 152911614'-(Aminomethyl)-biphenyl-2-carboxylic acid

Product 1

HCID 152911634'-[[(2,6-Dichloro-4-quinazolinyl)amino]methyl][1,1'-biphenyl]-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of sodium acetate (0.56 g), 2,4,6-trichloroquinazoline (0.40 g) and 4'-aminomethyl (1,1'-biphenyl)-2-carboxylic acid (0.43 g) was stirred at room temperature in 10 mL of THF for 5 days. All solvents were removed by evaporation and the resulting residue was partitioned between ethyl acetate and brine. The ethyl acetate fraction was dried over anhydrous magnesium sulfate, filtered and evaporated. The crude material was purified using silica gel chromatography to yield 0.15 g (21%) of an off white solid (m.p.=210°-240° C.): 1H NMR (DMSO-d6, 400 MHz) δ9.45 (t, J=6.2 Hz, 1H), 8.52 (d, J=2.3 Hz, 1H), 7.83 (dd, J=2.3, 8.9 Hz, 1H), 7.66 (m, 2H), 7.49 (m, 1H), 7.35 (m, 7H), 4.77 (d, J=5.2 Hz); negative FAB MS m/e 422(M-H). Anal. calcd for C 22 H15Cl2N3O2 : C, 62.28; H, 3.56; N, 9.90. Found: C, 62.44; H, 3.52; N, 9.95.

Workup

  1. customAll solvents were removed by evaporation
  2. customthe resulting residue was partitioned between ethyl acetate and brine
  3. dry with materialThe ethyl acetate fraction was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-d39f35cb53434341bb10c433fce7dfe1
Source dataset
uspto-grants-1993_02
Patent number
US05187168

Reaction notes

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