Acetic Acid → HCID 178422299, compound

HRID 1056972Notes

Reaction equation

HRID 1056972 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.C(O)(=O)C.[Br:12][CH:13]([C:19](=O)[CH3:20])[C:14](OCC)=[O:15]>C(OCC)C>[Br:12][C:13]1[C:19]([CH3:20])=[N:7][C:5]2[N:4]([N:3]=[C:2]([CH3:1])[CH:6]=2)[C:14]=1[OH:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11206579Ethyl 2-bromo-3-oxobutanoateHCID 178418690HCID 178418690, compound

Product 1

HCID 178422299HCID 178422299, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-methyl-1H-pyrazol-5-amine (0.186 g, 1.92 mmol) and acetic acid (3.71 mL, 65.2 mmol) was slightly heated until complete dissolution and the resultant solution was cooled to RT and mixed with ethyl 2-bromo-3-oxobutanoate (1.20 g, 5.74 mmol). The resultant reaction mixture was stirred at RT for 16 h, after which time the reaction mixture was diluted with diethyl ether, cooled to 0° C. and stirred at that temperature for 30 min. The white solid precipitate was separated by filtration and washed with cold diethyl ether and dried to give the desired product (363 mg, 78%) as a white solid. LCMS calculated for C8H9BrN3O (M+H)+: m/z=242.0, 244.0. found: 241.9, 244.0.

Workup

  1. temperaturewas slightly heated until complete dissolution
  2. customThe resultant reaction mixture
  3. temperaturecooled to 0° C.
  4. stirringstirred at that temperature for 30 min
  5. customThe white solid precipitate was separated by filtration
  6. washwashed with cold diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-b09f5e393afb4ac58d2a499dfc9d06d5
Source dataset
uspto-grants-2016_07
Patent number
US09399640B2

Reaction notes

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