Trifluoroacetic acid → HCID 11744059、化合物

HRID 853658ノート

反応式

HRID 853658 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:17]=2[C:18]([O:33]C(C2C=CC=CC=2)C2C=CC=CC=2)=[C:19]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][C:20]=12)=[O:10].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:17]=2[C:18]([OH:33])=[C:19]2[C:23](=[O:24])[N:22]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:21][C:20]=12)=[O:10]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928799HCID 58928799、化合物

生成物 1

HCID 11744059HCID 11744059、化合物収率 56.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Carboxamide 231 (0.225 g, 0.355 mmol) was dissolved in 1 mL of dichloromethane. To this was added 0.5 mL of triethylsilane and 0.25 mL of trifluoroacetic acid. Stirred at room temperature and after ten minutes complete by TLC. Concentrated off volatiles, azeotroped with toluene to give crude. Triturated twice with 1:1 diethyl ether/hexanes to give 7-(4-fluoro-benzyl)-9-hydroxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinoline-5-carboxylic acid (pyridin-2-ylmethyl)-amide 232 (0.11 g, 0.20 mmol, 56%.) 1H NMR (CD3SOCD3) δ 9.18 (s, 1H), 8.96 (d, 1H), 8.65 (dd, 2H), 8.09 (dd, 1H), 7.76 (dd, 1H), 7.64 (dd, 1H), 7.36 (dd, 2H), 7.22 (dd, 2H), 4.70 (s, 4H), 4.54 (s, 2H). 19F NMR: −75.37 MS: 443 (M+1), 441 (M−1)

後処理

  1. concentrationConcentrated off volatiles
  2. customazeotroped with toluene
  3. customto give crude
  4. customTriturated twice with 1:1 diethyl ether/hexanes

出典と根拠

ORDレコード
ord-7b998883f13a448998d752fa6f98d87d
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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