Trifluoroacetic acid → HCID 58928763、化合物

HRID 853656ノート

反応式

HRID 853656 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]3[CH:18]=[CH:19][CH:20]=[N:21][C:22]=3[C:23]([O:38]C(C3C=CC=CC=3)C3C=CC=CC=3)=[C:24]3[C:28](=[O:29])[N:27]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:26][C:25]=23)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[F:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:27]2[C:28](=[O:29])[C:24]3[C:23]([OH:38])=[C:22]4[C:17]([CH:18]=[CH:19][CH:20]=[N:21]4)=[C:16]([C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[O:15])[C:25]=3[CH2:26]2)=[CH:32][CH:33]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 12052TriethylsilaneHCID 58928973HCID 58928973、化合物

生成物 1

HCID 58928763HCID 58928763、化合物収率 445.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Carboxamide 229 (0.0108 g, 0.0153 mmol) was dissolved in 1 mL of dichloromethane. To this was added 0.4 mL of triethylsilane and 0.2 mL of trifluoroacetic acid. Stirred at room temperature and after ten minutes complete by TLC. Concentrated off volatiles, azeotroped with toluene to give crude. Then dissolved in 0.6 mL dichloromethane, 0.6 ml trifluoroacetic acid. Stirred at room temperature for one hour. 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-5-(piperazine-1-carbonyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 230 (0.039 g, 0.0682 mmol, 100%.) 1H NMR (CD3SOCD3) δ 98.97 (s, 2H), 8.32 (d, 1H), 7.74 (s, 1H), 7.36 (dd, 2H), 7.19 (dd, 2H), 4.86 (d, 1H), 4.58 (d, 1H), 4.42 (d, 1H), 4.34 (d, 1H), 3.9-2.90 (m, 8H.) 19F NMR: −74.202 MS: 421 (M+1), 419 (M−1)

後処理

  1. concentrationConcentrated off volatiles
  2. customazeotroped with toluene
  3. customto give crude
  4. stirringStirred at room temperature for one hour
  5. concentrationConcentrated off volatiles
  6. customazeotroped with toluene
  7. customto give crude
  8. customTriturated twice with 1:1 diethyl ether/hexanes

出典と根拠

ORDレコード
ord-f73bf428fda94dc38065bf5cbc396d7a
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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