Ethanol → HCID 90011170, compound

HRID 1481486Notes

Reaction equation

HRID 1481486 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]([NH:19][NH2:20])=[O:18])=[N:9]2)=[N:6][CH:7]=1.Br[C:22]1[CH:23]=CC(N2C(C(F)(F)F)=CC(C(OCC)=O)=N2)=N[CH:27]=1.O.NN.[CH2:45]([OH:47])[CH3:46]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([F:14])([F:16])[F:15])=[CH:11][C:10]([C:17]3[O:18][C:22]([CH3:23])([CH3:27])[N:20]([C:45](=[O:47])[CH3:46])[N:19]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 90011092HCID 90011092, compoundHCID 90011236HCID 90011236, compound

Product 1

HCID 90011170HCID 90011170, compoundYield 95%

Conditions

Temperature
100 °C

Procedure

Step-1: 1-(5-Bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carbohydrazide: A mixture of ethyl 1-(5-bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate (33 g, 91 mmol) and hydrazine hydrate (17.07 mL, 544 mmol) in ethanol (330 mL) was heated at 100° C. overnight. The reaction mixture was cooled back down to room temperature and the solvent was evaporated under vacuum. The residue was triturated with toluene to obtain 30 g (95%) of the title compound as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 9.97 (s, 1H, D2O exchangeable), 8.72 (d, J=2.5 Hz, 1H), 8.40 (dd, J=2.5 & 8.5 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.54 (s, 1H), 4.58 (s, 2H, D2O exchangeable); ESI-MS (m/z) 350, 352 [(MH)+, Br79,81].

Workup

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

Sources & evidence

ORD record
ord-619902ea9f664535aeae4a495d5bde47
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

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