Trifluoroacetic acid → HCID 59729939, compound

HRID 131029Notes

Reaction equation

HRID 131029 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. Solubolize 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 NH3MeOH 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. additionSolubolize 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 NH3MeOH

Sources & evidence

ORD record
ord-77f81df1462c4fd3af2959d556652720
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

Loading…