Ammonium Hydroxide → HCID 18446617, compound

HRID 1269083Notes

Reaction equation

HRID 1269083 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([F:20])[CH:15]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)=O.[C:21]([NH2:24])(=[S:23])[CH3:22].[OH-].[NH4+]>CN(C)C=O>[F:20][C:16]1[CH:15]=[C:14]([C:13]2[C:5]([C:3]3[N:24]=[C:21]([CH3:22])[S:23][CH:2]=3)=[N:6][N:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=23)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 2723949ThioacetamideHCID 18446614HCID 18446614, compound

Product 1

HCID 18446617HCID 18446617, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-1-[3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-2-yl]ethanone (250 mg, 0.75 mmol) in N,N-dimethylformamide (15 mL) was added thioacetamide (67 mg, 0.90 mmol). After heating at 60° C. for 3 hours, the reaction was cooled to room temperature. An ammonium hydroxide solution was used to adjust the pH to 9. The resultant solution was extracted with ethyl acetate. The organics were combined and washed with water, brine and dried over magnesium sulfate. Filtration and concentration gave 3-(2-fluoro-4-pyridinyl)-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridine (220 mg, 95%) as a pale yellow solid. 1H NMR (CDCl3): δ 8.56 (d, 1H), 8.23 (d, 1H), 7.61 (d, 1H), 7.30 (s, 1H), 7.27 (m, 2H), 7.05 (s, 1H), 6.89 (m, 1H), 2.76 (s, 3H). MS m/z 311 (M+1).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionThe resultant solution was extracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a3be4c5841874a34a74cd9102bb22623
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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