Hydrochloric Acid → HCID 59310047, compound

HRID 1513078Notes

Reaction equation

HRID 1513078 reaction equation
[C:1]([CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([F:22])[C:15]=2[F:23])=[CH:10][C:9]([N:24]2[C:32](=[O:33])[NH:31][C:30]3[C:25]2=[N:26][C:27]([CH3:36])=[N:28][C:29]=3[O:34][CH3:35])=[C:8]([Cl:37])[CH:7]=1)(O)=[O:2].[C:38](N1C=CN=C1)([N:40]1C=CN=C1)=O.CN.Cl>O1CCCC1>[Cl:37][C:8]1[C:9]([N:24]2[C:32](=[O:33])[NH:31][C:30]3[C:25]2=[N:26][C:27]([CH3:36])=[N:28][C:29]=3[O:34][CH3:35])=[CH:10][C:11]([O:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([F:22])[C:15]=2[F:23])=[C:6]([CH:7]=1)[O:5][CH2:4][C:1]([NH:40][CH3:38])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59309941HCID 59309941, compound

Product 1

HCID 59310047HCID 59310047, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-[4-carboxymethoxy-2-chloro-5-(2,3-difluoro-6-methoxy-benzyloxy)phenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (80 mg) in tetrahydrofuran (2 mL) was added 1,1′-carbonyldiimidazole (48 mg), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added methylamine (40% methanol solution, 1 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 2 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=6/1) to give the title compound (63 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=6/1)

Sources & evidence

ORD record
ord-7a479bed791e4b8e8f181b2c583b48f6
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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