Sodium hydride → 4-(1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206145Notes

Reaction equation

HRID 2206145 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:12]3[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[S:15][CH:16]=3)=[N:10][NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1.[H-].[Na+].CC1C=CC(S(O[CH:33]2[CH2:42][CH2:41][C:36]3([O:40][CH2:39][CH2:38][O:37]3)[CH2:35][CH2:34]2)(=O)=O)=CC=1>CN(C=O)C>[O:37]1[C:36]2([CH2:41][CH2:42][CH:33]([N:11]3[C:7]4[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=4[C:9]([C:12]4[CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[S:15][CH:16]=4)=[N:10]3)[CH2:34][CH2:35]2)[O:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)HCID 1179879184-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-Thiophenecarboxamide

Product 1

HCID 1179885934-(1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamideYield 54.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide (65.0 mg) in DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil, 19.0 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1,4-dioxaspiro[4.5]dec-8-yl 4-methylbenzenesulfonate (148 mg), 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 (hexane/ethyl acetate) to give the title compound (53.9 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 (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-65da43478e3e4cd983c1f41c3e3ac260
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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