HCID 10136135, compound → HCID 10180698, compound

HRID 351731Notes

Reaction equation

HRID 351731 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:42].[Mg+2]>C(Cl)Cl.CO>[CH:1]([NH:4][C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][C:26]3[CH:27]=[CH:28][N+:29]([O-:42])=[CH:30][CH:31]=3)[CH:19]=2)[CH:8]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 10136135HCID 10136135, compoundHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)2×

Product 1

HCID 10180698HCID 10180698, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Isopropyl-1-[3-(4-pyridinylethynyl)phenyl]-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide from EXAMPLE 3 in methylene chloride (36 mL/mmol) and methanol (3 mL/mmol) was added magnesium monoperoxyphthalate hexahydrate (MMPP, 3.6 eq) and the mixture was stirred at room temperature overnight. A further amount of MMPP (2 eq) was added and stirring was continued for 24 hours. The resulting mixture was filtered through a bed of celite, the filtrate was diluted with methylene chloride and washed with aqueous sodium bicarbonate and water. After drying, the organic phase was evaporated and the crude product was purified by chromatography on silica gel eluting with 10% methanol in methylene chloride to afford the title compound as a solid.

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. filtrationThe resulting mixture was filtered through a bed of celite
  4. additionthe filtrate was diluted with methylene chloride
  5. washwashed with aqueous sodium bicarbonate and water
  6. customAfter drying
  7. customthe organic phase was evaporated
  8. customthe crude product was purified by chromatography on silica gel eluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-5e236ad8aab548618facbd37fb6edc01
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Reaction notes

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