Acetamide → HCID 68512552, compound

HRID 2063254Notes

Reaction equation

HRID 2063254 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[C:24]([NH2:27])(=[O:26])[CH3:25].[H-].[Na+]>CN(C)C=O>[F:23][C:20]1[CH:21]=[CH:22][C:17]([C:9]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:27][C:24](=[O:26])[CH3:25])[N:7]=3)=[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 24758Sodium hydrideHCID 86646911HCID 86646911, compound2×

Product 1

HCID 68512552HCID 68512552, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-chloro-4-pyrimidinyl)-2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (i.e. the product of Step B) (0.10 g, 0.27 mmol), acetamide (0.08 g, 1.3 mmol), molecular sieves (4 Å, 3.0 g) in 4 mL of N,N-dimethylformamide was stirred at room temperature for 15 minutes. Sodium hydride (55% dispersion, 0.06 g, 1.3 mmol) was added, and the reaction mixture was heated at 100° C. overnight. The reaction mixture was then filtered though a pad of Celite® diatomaceous filter aid, and then concentrated under reduced pressure. The crude oil was purified by medium-pressure liquid chromatography on silica gel using 0-100% of ethyl acetate in hexanes as eluant to give 55 mg of the title compound, a compound of the present invention, as an oil.

Workup

  1. temperaturethe reaction mixture was heated at 100° C. overnight
  2. filtrationThe reaction mixture was then filtered though a pad of Celite® diatomaceous filter aid
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil was purified by medium-pressure liquid chromatography on silica gel using 0-100% of ethyl acetate in hexanes as eluant

Sources & evidence

ORD record
ord-0847f295a7bf4880b58a1b41446c1e4b
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

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