Sodium Acetate → 4'-[[[5,6,7,8-Tetrahydro-2-(trifluoromethyl)-4-quinazolinyl]amino]methyl][1,1'-biphenyl]-2-carboxylic acid

HRID 2254119ノート

反応式

HRID 2254119 の反応式
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.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([C:30]([OH:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1.C([O-])(=O)C.[Na+]>C(O)CCC>[F:13][C:12]([F:15])([F:14])[C:4]1[N:3]=[C:2]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([C:30]([OH:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 152911614'-(Aminomethyl)-biphenyl-2-carboxylic acidHCID 19383098HCID 19383098、化合物

生成物 1

HCID 98465354'-[[[5,6,7,8-Tetrahydro-2-(trifluoromethyl)-4-quinazolinyl]amino]methyl][1,1'-biphenyl]-2-carboxylic acid収率 59%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

To 10 mL of n-butanol were added 0.526 g of 4-chloro-5,6,7,8-tetrahydro-2-trifluoromethylquinazoline, 0.408 g of 4' aminomethyl-(1,1'-biphenyl)-2-carboxylic acid and 1.1 g of sodium acetate. The resulting mixture was refluxed for 3 days, cooled to room temperature and all solvents were removed by evaporation. The residue was taken up in ethyl acetate and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to yield an off-white solid which was purified by silica chromatography to yield the desired product (0.39 g, 59%). The compound was characterized as its sodium salt: 1H NMR (DMSO-d6, 400 MHz) δ 7.88 (t, J=6.0 Hz, 1H), 7.39 (m, 2H), 7.28 (m, 3H), 7.17 (m, 3H), 4.60 (d, J=5.9 Hz, 2H), 2.61 (m, 2H), 2.38 (m, 2H), 1.74 (m, 4H); negative FAB-MS m/e 448(M-H), 426(M-Na). Anal. calcd for C23H19F3N3NaO2.1.0H2O: C, 59.10; H, 4.53; N, 8.99. Found: C, 59.03; H, 4.48; N, 9.09.

後処理

  1. temperatureThe resulting mixture was refluxed for 3 days
  2. customall solvents were removed by evaporation
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto yield an off-white solid which
  8. customwas purified by silica chromatography

出典と根拠

ORDレコード
ord-5a776dd3f8a24279b7d8ffee0bf0f075
出典データセット
uspto-grants-1993_08
特許番号
US05234936

反応ノート

読み込み中…