4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole → 3-(3-(4-(3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazol-4-ylmethyl)-3-methylphenoxy)propylamino)propionamide

HRID 2189414Notes

Reaction equation

HRID 2189414 reaction equation
C([N:8]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:42][C@H:41]([CH2:43][OH:44])[C@@H:39]([OH:40])[C@H:37]([OH:38])[C@H:35]3[OH:36])=[N:27][NH:28][C:29]=2[CH:30]([CH3:32])[CH3:31])=[C:20]([CH3:45])[CH:19]=1)[CH2:9][CH2:10][C:11](=[O:13])[NH2:12])C1C=CC=CC=1>CO.[C].[Pd]>[C:11]([CH2:10][CH2:9][NH:8][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:42][C@H:41]([CH2:43][OH:44])[C@@H:39]([OH:40])[C@H:37]([OH:38])[C@H:35]3[OH:36])=[N:27][NH:28][C:29]=2[CH:30]([CH3:32])[CH3:31])=[C:20]([CH3:45])[CH:19]=1)(=[O:13])[NH2:12]

Participants

4

Reactant 1

HCID 689413124-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Product 1

HCID 100528963-(3-(4-(3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazol-4-ylmethyl)-3-methylphenoxy)propylamino)propionamideYield 19.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole (0.5 g) was dissolved in methanol (8 mL). To the solution was added 10% palladium-carbon powder (0.1 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. A part (0.1 g) of the residue was dissolved in a mixed solvent of methanol (1 mL) and ethyl acetate (1.5 mL). To the solution was added a seed crystal, and the mixture was stirred at room temperature for 3 days. The precipitated crystals were collected by filtration. The crystals were washed with a mixed solvent of methanol and ethyl acetate (2/3), and dried under reduced pressure to give the title compound (85 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionA part (0.1 g) of the residue was dissolved in a mixed solvent of methanol (1 mL) and ethyl acetate (1.5 mL)
  4. additionTo the solution was added a seed crystal
  5. stirringthe mixture was stirred at room temperature for 3 days
  6. filtrationThe precipitated crystals were collected by filtration
  7. washThe crystals were washed with a mixed solvent of methanol and ethyl acetate (2/3)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-40857f26667e4c0f9e9c9a5419010907
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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