Trifluoroacetic acid → HCID 59729939, compound

HRID 228482Notes

Reaction equation

HRID 228482 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][N:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH2:26])=[O:27])=[CH:21][N:20]=2)[CH2:16][CH2:17][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59729912HCID 59729912, compound

Product 1

HCID 59729939HCID 59729939, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 8-(5-Carbamoyl-pyridin-2-yloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (249.6 mg, 1.01 mmol), CH2Cl2 (25 ml), and TFA (10 ml) at room temperature under nitrogen atmosphere. After the reaction stirs for 12 hours then concentrate under reduced pressure. Solubilize the mixture in MeOH and add to a 2 g SCX Column (pre-treated with 5% AcOH-MeOH), wash several times with MeOH, and elute the product with 1N NH3 MeOH to afford 156.1 mg, 0.58 mmol (57% yield) of the title compound.

Workup

  1. customat room temperature
  2. concentrationthen concentrate under reduced pressure
  3. additionSolubilize the mixture in MeOH and add to a 2 g SCX Column (pre-treated with 5% AcOH-MeOH)
  4. washwash several times with MeOH
  5. washelute the product with 1N NH3 MeOH

Sources & evidence

ORD record
ord-24b179e53a3c442ea9f0a8eb13425911
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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