Dichloromethane → HCID 59730015, compound

HRID 228478Notes

Reaction equation

HRID 228478 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 1 M 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, 1 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, 1 g SCX columns
  8. washwash with MeOH
  9. washelute with 1N NH3 MeOH
  10. concentrationConcentrate

Sources & evidence

ORD record
ord-965b08f1656d41d3917668c7b945e79d
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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