Trifluoroacetic acid → HCID 58928763, 화합물

HRID 853656노트

반응식

HRID 853656 반응식
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

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 12052TriethylsilaneHCID 58928973HCID 58928973, 화합물

생성물 1

HCID 58928763HCID 58928763, 화합물수율 445.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f73bf428fda94dc38065bf5cbc396d7a
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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