Ethanol → HCID 90011193, compound

HRID 1481481Notes

Reaction equation

HRID 1481481 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17](=O)[C:18]([CH3:24])([CH3:23])[C:19]([NH:21][NH2:22])=[O:20])=[N:9]2)=[N:6][CH:7]=1.O.NN.[CH2:29](O)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]3[C:18]([CH3:24])([CH3:23])[C:19](=[O:20])[N:21]([CH3:29])[N:22]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 90011140HCID 90011140, compound

Product 1

HCID 90011193HCID 90011193, compoundYield 86%

Conditions

Temperature
80 °C

Procedure

Step-2: 3-(1-(5-Bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-3-yl)-2,2-dimethyl-3-oxopropanehydrazide: A mixture of step-1 intermediate (2.40 g, 5.53 mmol) and hydrazine hydrate (0.87 mL, 27.6 mmol) in ethanol (30 mL) was heated at 80° C. overnight. The reaction mixture was cooled to room temperature and the solvent was then evaporated under vacuum. The residue was triturated with toluene to obtain 2.0 g (86%) of title compound as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H, D2O exchangeable), 8.72 (d, J=2.0 Hz, 1H), 8.38 (dd, J=2.0 & 8.0 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.54 (s, 1H), 1.42 (s, 6H); ESI-MS (m/z) 420, 422 [(MH)+, Br79,81].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was then evaporated under vacuum
  3. customThe residue was triturated with toluene

Sources & evidence

ORD record
ord-f3f6fdbd62b14c7b875dc0978e6ec4e5
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

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