Trifluoroacetic acid → HCID 59729939, compound

HRID 130936Notes

Reaction equation

HRID 130936 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. Stir 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 with 1.0 N NH3 in 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 with 1.0 N NH3 in MeOH

Sources & evidence

ORD record
ord-10c31a0f1d4d45299c75c8b22ca3b5e6
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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