HCID 57652582, compound → 7-Bromo-6-(piperidin-4-yloxy)-2H-isoquinolin-1-one

HRID 1930222Notes

Reaction equation

HRID 1930222 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Br:25])[C:21](=[O:26])[N:20](CC2C=CC(OC)=CC=2)[CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O>[Br:25][C:24]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][NH:20][C:21]2=[O:26])=[CH:16][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 57652582HCID 57652582, compound

Product 1

HCID 576523477-Bromo-6-(piperidin-4-yloxy)-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
140 °C

Procedure

182 mg 4-[7-bromo-2-(4-methoxy-benzyl)-1-oxo-1,2-dihydro-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester (314) were dissolved in 5 mL of trifluoroacetic acid. After 2 h at room temperature, the mixture was heated at 140° C. in a microwave for 2 h. The solvent was removed i. vac. and the residue was dissolved 2 N HCl. The aqueous solution was washed twice with dichloromethane and the organic layers were extracted with 2 N HCl. The combined aqueous solutions were evaporated i. vac. and the residue was dissolved in water. After lyophilization the title compound was isolated as HCl-salt. Rt=0.80 min (Method B). Detected mass: 323.1/325.1 (M+H+).

Workup

  1. customThe solvent was removed i
  2. dissolutionand the residue was dissolved 2 N HCl
  3. washThe aqueous solution was washed twice with dichloromethane
  4. extractionthe organic layers were extracted with 2 N HCl
  5. customThe combined aqueous solutions were evaporated i
  6. dissolutionand the residue was dissolved in water

Sources & evidence

ORD record
ord-6fa2afee6fdb42aa84377a9fb028f9d0
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

Loading…