Hydrochloric Acid → HCID 59310140, compound

HRID 1513079Notes

Reaction equation

HRID 1513079 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]=[CH:16][C:15]=2[F:22])=[CH:10][C:9]([N:23]2[C:31](=[O:32])[NH:30][C:29]3[C:24]2=[N:25][C:26]([CH2:35][OH:36])=[N:27][C:28]=3[O:33][CH3:34])=[C:8]([Cl:37])[CH:7]=1)([OH:3])=O.CN.Cl.[CH2:41]([N:43]=C=NCCCN(C)C)C.Cl>CN(C)C=O.C(N(CC)CC)C>[Cl:37][C:8]1[C:9]([N:23]2[C:31](=[O:32])[NH:30][C:29]3[C:24]2=[N:25][C:26]([CH2:35][OH:36])=[N:27][C:28]=3[O:33][CH3:34])=[CH:10][C:11]([O:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[F:22])=[C:6]([CH:7]=1)[O:5][CH2:4][C:1]([NH:43][CH3:41])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59310074HCID 59310074, compound

Product 1

HCID 59310140HCID 59310140, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 9-[4-carboxymethoxy-2-chloro-5-(2-fluoro-6-methoxybenzyloxy)-phenyl]-2-hydroxymethyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.1 g), 40% aqueous methylamine solution (0.06 mL), 1-hydroxybenzo[r]azole monohydrate (34 mg) and triethylamine (0.1 mL) in N,N-dimethylformamide (2 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (72 mg), and the mixture was stirred at 60° C. overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 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=9/1) to give the title compound (54 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=9/1)

Sources & evidence

ORD record
ord-3c21d29c99bd4789a1a62fdf04c09055
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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