Trifluoroacetic acid → 2-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acid

HRID 1692471Notes

Reaction equation

HRID 1692471 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][C:13]([CH:15]1[CH2:19][CH:18]([O:20][C:21]2[C:30]3[C:25](=[C:26]([CH3:33])[C:27]([O:31][CH3:32])=[CH:28][CH:29]=3)[N:24]=[C:23]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[N:35]=3)[CH:22]=2)[CH2:17][CH:16]1[C:41](=[O:53])[NH:42][C:43]1([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:45][CH:44]1[CH:46]=[CH2:47])=[O:14])(C)(C)C.C([SiH](CC)CC)C>C(Cl)Cl>[CH2:51]([O:50][C:48]([C:43]1([NH:42][C:41]([CH:16]2[CH2:17][CH:18]([O:20][C:21]3[C:30]4[C:25](=[C:26]([CH3:33])[C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[C:23]([C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([CH3:40])[N:35]=4)[CH:22]=3)[CH2:19][CH:15]2[C:13]([OH:14])=[O:12])=[O:53])[CH2:45][CH:44]1[CH:46]=[CH2:47])=[O:49])[CH3:52]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 668713072-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acid tert-butyl ester

Product 1

HCID 668720342-(1-Ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acidYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (24 mL) was added at room temperature to a solution of 2-(1-ethoxycarbonyl-2-vinylcyclopropylcarbamoyl)-4-[2-(6-methyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]cyclopentanecarboxylic acid tert-butyl ester (98, 1.1 g, 1.75 mmol) and triethylsilane (510 mg, 2.5 eq) in CH2Cl2 (24 mL). After 2 h, the reaction mixture was concentrated under reduced pressure, and then co-evaporated with toluene. The residue was re-dissolved in AcOEt and successively washed with a solution of NaHCO3 and brine. The organic layer was dried (MgSO4), filtered and evaporated, to give 800 mg (80%) of the title compound 99 (800 mg, 80%): m/z=574 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was re-dissolved in AcOEt
  3. washsuccessively washed with a solution of NaHCO3 and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1404697d282346d28a99c6cda45682ab
Source dataset
uspto-grants-2012_04
Patent number
US08153800B2

Reaction notes

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