Dichloromethane → HCID 59730015, compound

HRID 131025Notes

Reaction equation

HRID 131025 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][N:20]=3)[CH:14]=2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([NH2:26])=[O:27])=[CH:21][N:20]=3)=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59730107HCID 59730107, compound

Product 1

HCID 59730015HCID 59730015, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Combine 6-(5-Carbamoyl-pyridin-2-yloxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (4.0 g, 10.83 mmol), CH2Cl2 (100 mL), and TFA (25 mL). After reaction stirs at room temperature for 12 hours, add 1M K2CO3 and CHCl3 to the reaction. Separate the organic layer, wash with brine, and dry over Na2SO4. Concentrate under reduced pressure and add mixture to 2, 10 g SCX columns, wash with MeOH, and elute with 1N NH3 MeOH. Concentrate to afford 2.91 g, 10.8 mmol (71% yield) of the title compound as a white foam: 1H NMR (500 MHz, DMSO); 2.9-3.1 (2H, m), 3.2-3.5 (2H, m), 4.2-4.4 (2H, m), 6.9-7.2 (3H, m), 7.2-7.4 (1H, m), 7.4-7.6 (1H, m), 7.9-8.1 (1H, m), 8.2-8.4 (1H, m), 8.5-8.7 (1H, m), 8.2-9.4 (2H, m); MS m/z 269 (M+1).

Workup

  1. customAfter reaction stirs at room temperature for 12 hours
  2. customto the reaction
  3. customSeparate the organic layer
  4. washwash with brine
  5. dry with materialdry over Na2SO4
  6. concentrationConcentrate under reduced pressure
  7. additionadd mixture to 2, 10 g SCX columns
  8. washwash with MeOH
  9. washelute with 1N NH3 MeOH
  10. concentrationConcentrate

Sources & evidence

ORD record
ord-41e34e9e6bb143cf9118280e4b4cffd8
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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