Sodium Acetate → 5,6,7,8-tetrahydro-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2-(trifluoromethyl)-4-quinazolinamine

HRID 2254120Notes

Reaction equation

HRID 2254120 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=1.Cl.[NH:17]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[CH:30][CH:29]=2)=[N:20][N:19]=[N:18]1.C([O-])(=O)C.[Na+]>C(O)CCC.CO>[NH:20]1[C:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:2]3[C:11]4[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=4[N:5]=[C:4]([C:12]([F:15])([F:14])[F:13])[N:3]=3)=[CH:30][CH:29]=2)=[N:17][N:18]=[N:19]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 19383098HCID 19383098, compoundHCID 178479176(4-(2-(1H-1,2,3,4-tetrazol-5-yl)phenyl)phenyl)methanamine hydrochloride

Product 1

HCID 1785062715,6,7,8-tetrahydro-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-2-(trifluoromethyl)-4-quinazolinamineYield 50%

Reagents, catalysts & solvents 1

HCID 22439470n-Butanol methanolSolvent

Procedure

To 10 mL of a 5:1 mixture of n-butanol/methanol were added 1.42 g of 4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazoline, 1.73 g of N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amine hydrochloride and 2.7 g of sodium acetate. The resulting mixture was heated at reflux for 5 days and then cooled to room temperature. All solvents were removed by evaporation and the resulting residue was purified on silica to yield 1.35 g (50%) of the desired product. The compound was characterized as its potassium salt: 1H NMR (DMSO-d6, 400 MHz) δ 7.78 (t, J=6.0 Hz, 1H), 7.50 (m, 1H), 7.32 (m, 3H), 7.15 (m, 2H), 7.03 (m, 2H), 4.57 (d, J=6.0 Hz, 2H), 2.61 (m, 2H), 2.38 (m, 2H, 1.75 (m, 4H); negative FAB-MS m/e 488(M-H), 450(M-K). Anal. calcd for C23H19F3KN7.0.5H2O: C, 55.41; H, 4.04; N, 19.67. Found: C, 55.66; H, 4.09; N, 19.46.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 days
  3. customAll solvents were removed by evaporation
  4. customthe resulting residue was purified on silica

Sources & evidence

ORD record
ord-d3ac053826f042e5814d039675b47709
Source dataset
uspto-grants-1993_08
Patent number
US05234936

Reaction notes

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