Trifluoroacetic acid → HCID 58928763, compound

HRID 853656Notes

Reaction equation

HRID 853656 reaction equation
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

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 58928973HCID 58928973, compound

Product 1

HCID 58928763HCID 58928763, compoundYield 445.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-f73bf428fda94dc38065bf5cbc396d7a
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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