Ammonium Acetate → HCID 58515974, compound

HRID 717858Notes

Reaction equation

HRID 717858 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([N:18]=[CH:19][CH:20]=2)[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO>[Cl:1][C:2]1[C:3]2[N:4]([N:18]=[CH:19][CH:20]=2)[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[C:6]([CH:8]([NH2:27])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 517165Ammonium Acetate2×HCID 5003444Sodium cyanoborohydride2×HCID 58516000HCID 58516000, compound

Product 1

HCID 58515974HCID 58515974, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

The mixture of 1-[4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]ethanone (0.2 g, 0.7 mmol) in methanol (7.0 mL) and the ammonium acetate (0.5340 g, 6.928 mmol) was heated at 65° C. for 1 hour, all solids dissolved. The sodium cyanoborohydride (0.1306 g, 2.078 mmol) was added and the solution was heated at 65° C. overnight. The reaction was incomplete, additional ammonium acetate and sodium cyanoborohydride were added and the reaction was stirred for another 18 hours. This was allowed to cool to room temperature, concentrated in vacuo, taken up in ethyl acetate and washed with a small amount of water, brine, dried over magnesium sulfate and concentrated to give 1-[4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]ethanamine (0.18 g, 90%) as a viscous oil. LCMS calculated for C15H14ClFN3 (M+H)+: m/z=290.1. found: 289.9.

Workup

  1. dissolutionall solids dissolved
  2. temperatureto cool to room temperature
  3. concentrationconcentrated in vacuo
  4. washwashed with a small amount of water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ad48bc10fed44dd295daf6954a2fe9b7
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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