Trifluoroacetic acid → HCID 178446056, compound

HRID 2121249Notes

Reaction equation

HRID 2121249 reaction equation
C([N:20]1[CH:24]=[C:23]([CH2:25][NH:26][C:27]2[C:28]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[C:29]([CH:41]=[CH:42][CH:43]=2)[C:30]([C:32]([CH3:40])([CH3:39])[CH2:33][C@@H:34]([C:36]([OH:38])=[O:37])[NH2:35])=[O:31])[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[NH:20]1[CH:24]=[C:23]([CH2:25][NH:26][C:27]2[C:28]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)=[C:29]([CH:41]=[CH:42][CH:43]=2)[C:30]([C:32]([CH3:40])([CH3:39])[CH2:33][C@@H:34]([C:36]([OH:38])=[O:37])[NH2:35])=[O:31])[N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69891833HCID 69891833, compound

Product 1

HCID 178446056HCID 178446056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 387B (0.25 g, 0.38 mmol) was dissolved in 10 mL dichloromethane and 3 mL trifluoroacetic acid followed by the addition of 1.5 mL of triethylsilane and the reaction stirred at room temperature for 2 hours. The solvents were evaporated and ether added followed by the addition of 6 N HCl in ether to precipitate the desired compound (0.12 g, 77%) which was collected by rapid filtration. 1H NMR (300 MHz, DMSO-d6) 0.76 (dd, 6H), 1.38 (m, 2H), 1.55 (m, 1H), 4.19 (m, 1H), 4.42 (d, 2H), 6.63 (s, 1H), 6.73 (d, 1H), 7.31-7.36 (m, 6H), 7.63 (s, 1H), 8.23 (d, 1H), 9.09 (s, 1H).

Workup

  1. customThe solvents were evaporated
  2. additionether added
  3. additionfollowed by the addition of 6 N HCl in ether
  4. customto precipitate the desired compound (0.12 g, 77%) which
  5. filtrationwas collected by rapid filtration

Sources & evidence

ORD record
ord-3276200691034ac785ab63b8d8ac3554
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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