Ethanol → HCID 90011519, compound

HRID 1481484Notes

Reaction equation

HRID 1481484 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:20])[NH:18][OH:19])=[N:9]2)=[N:6][CH:7]=1.Cl.NO.[C:24]([O-:27])([O-])=O.[Na+].[Na+].[CH2:30](O)C>>[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[N:20]([CH3:30])[C:24](=[O:27])[O:19][N:18]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 178513328HCID 178513328, compound

Product 1

HCID 90011519HCID 90011519, compoundYield 64%

Conditions

Temperature
85 °C

Procedure

Step-3: 1-(5-Bromopyridin-2-yl)-N-hydroxy-5-(trifluoromethyl)-1H-pyrazole-3-carboximidamide: A mixture of step-2 intermediate (150 mg, 0.473 mmol), hydroxylamine hydrochloride (82 mg, 1.183 mmol) and Na2CO3 (125 mg, 1.183 mmol) in ethanol (10 mL) was stirred at 85° C. for 6 h. Reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum. Water (10 mL) was added to the obtained residue and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 106 mg (64%) of the title compound as a white solid. 1HNMR (400 MHz, DMSO- d6) δ 9.96 (s, 1H), 8.69 (d, J=2.0 Hz, 1H), 8.37 (dd, J=2.0 & 8.0 Hz, 1H), 8.00 (d, J=8.0 Hz, 1H), 7.23 (s, 1H), 5.93 (s, 2H); ESI-MS (m/z) 350, 352 [(MH)+, Br79,81].

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customthe solvent was evaporated under vacuum
  4. additionWater (10 mL) was added to the obtained residue
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-374e0e18ae11472b98ed37e86dd95bd4
Source dataset
uspto-grants-2016_08
Patent number
US09409898B2

Reaction notes

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