HCID 58998406, compound → HCID 58998399, compound

HRID 1593082Notes

Reaction equation

HRID 1593082 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](=[O:20])[NH:14][CH:13]=[CH:12]2)C)(C)(C)C>CO.Cl.O=[Pt]=O>[F:19][C:18]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][NH:14][C:15]2=[O:20])=[CH:10][C:9]=1[NH:7][CH3:6]

Participants

5

Reactant 1

HCID 58998406HCID 58998406, compound

Product 1

HCID 58998399HCID 58998399, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 7-fluoro-1-oxo-1,2-dihydroisoquinolin-6-yl(methyl)carbamate (Example 45, 700 mg, 2.40 mmol) and PtO2 (470 mg) in MeOH (30 mL) containing concentrated HCl (8 drops) was hydrogenated under 300 psi in a high pressure vessel overnight. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. The residue was treated with TFA (10 mL) and stirred for 1 hr, after which, the TFA solution was concentrated in vacuo. The residue was purified by RP-HPLC to give the noted intermediate compound (142 mg). ES-MS (M+H)+=195.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was treated with TFA (10 mL)
  4. concentrationafter which, the TFA solution was concentrated in vacuo
  5. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-634b8f25aceb4b4ea211bfe168120266
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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