Ammonium Acetate → HCID 58368622, compound

HRID 1192712Notes

Reaction equation

HRID 1192712 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][N:6]2[CH3:22].C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH2:29])[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][N:6]2[CH3:22]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368633HCID 58368633, compound

Product 1

HCID 58368622HCID 58368622, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-7-(3,5-difluorophenyl)-1-methyl-1H-indazol-6-yl]ethanone (0.438 g, 1.36 mmol), ammonium acetate (1.05 g, 13.6 mmol) and sodium cyanoborohydride (0.172 g, 2.73 mmol) in methanol (5 mL) and acetonitrile (5 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, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness to give the desired product. LCMS calculated for C16H12ClF2N2 (M−NH2)+: m/z=305.1; Found: 305.0.

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-983544d287f547d0984af5989a00ab48
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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