Sodium hydride → 4-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206148Notes

Reaction equation

HRID 2206148 reaction equation
[O:1]=[C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[S:14][CH:15]=3)=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][NH:3]1.[H-].[Na+].CC1C=CC(S(O[CH:32]([CH2:36][CH3:37])[CH2:33][O:34][CH3:35])(=O)=O)=CC=1>CN(C=O)C>[CH3:35][O:34][CH2:33][CH:32]([N:10]1[C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=2[C:8]([C:11]2[CH:12]=[C:13]([C:16]([NH2:18])=[O:17])[S:14][CH:15]=2)=[N:9]1)[CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127007761-Methoxybutan-2-yl 4-methylbenzene-1-sulfonateHCID 1370107094-(4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

Product 1

HCID 1370105854-(1-(1-methoxybutan-2-yl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamideYield 32.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (50.0 mg) obtained in Step A of Example 141 in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil, 15.4 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1-methoxybutan-2-yl 4-methylbenzenesulfonate (99.0 mg) obtained in Step A-1 of Example 17, and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol) to give the title compound (21.8 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-52e7c3773fe941ac84f3815ff3b73c83
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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