Ammonium Acetate → HCID 58368591, compound

HRID 1192710Notes

Reaction equation

HRID 1192710 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=O)[CH3:12])[C:8]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH2:28])[CH3:12])[C:8]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368503HCID 58368503, compound

Product 1

HCID 58368591HCID 58368591, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-7-(3,5-difluorophenyl)-1H-indazol-6-yl]ethanone (0.20 g, 0.65 mmol) and ammonium acetate (0.50 g, 6.5 mmol) and sodium cyanoborohydride (0.082 g, 1.3 mmol) in methanol (2 mL) and acetonitrile (2 mL) was heated at 65° C. overnight in a sealed tube. The mixture was then cooled to room temperature and quenched with sat. sodium bicarbonate and then extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness to give the crude amine which was used directly in the next step. LCMS calculated for C15H10ClF2N2 (M−NH2)+: m/z=291.0; Found: 291.0.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with sat. sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-37e8c838e2fb421d9f2fc64654345e04
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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