Trifluoroacetic acid → HCID 86627570, compound

HRID 1970063Notes

Reaction equation

HRID 1970063 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[C:26]3[NH:33][CH:34]=[CH:35][C:25]=3[C:24]=2[CH:23]=1)=O)(C)(C)C.[CH2:36]([C:38]([O-:40])=[O:39])[CH3:37]>ClC(Cl)C>[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:31]=[CH:30][C:29]2[NH:28][C:27](=[O:32])[C:26]3[NH:33][CH:34]=[CH:35][C:25]=3[C:24]=2[CH:23]=1.[CH2:36]([C:38]([O-:40])=[O:39])[CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86627571HCID 86627571, compound

Product 1

HCID 86627570HCID 86627570, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

0.5 mL of trifluoroacetic acid is added to a solution of 100 mg (0.22 mmol) of 8-(2-tert-butoxycarbonylaminophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 2 mL of dichloroethane. The solution is stirred at room temperature for 30 minutes then the solvents are evaporated. The residue is triturated with diisopropyl ether then the solid is filtered and washed with dichloromethane. It is taken up in 2 mL of dichloromethane then triethylamine is added to release the amine. Water is added and the compound is extracted with dichloromethane. The organic phases are dried over magnesium sulfate, filtered and evaporated. The solid is triturated with water to give 35 mg (45%) of 8-(2-aminophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customthe solvents are evaporated
  2. customThe residue is triturated with diisopropyl ether
  3. filtrationthe solid is filtered
  4. washwashed with dichloromethane
  5. additiontriethylamine is added
  6. additionWater is added
  7. extractionthe compound is extracted with dichloromethane
  8. dry with materialThe organic phases are dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe solid is triturated with water

Sources & evidence

ORD record
ord-b5b3420ff91449cdb2158c587c63989f
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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