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Ethanol → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylmethylamino)pyrazole-3-carbonitrile

HRID 22865
Notes
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Reaction equation

HRID 22865 reaction equation
C(O)C.[BH4-].[Na+].[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[N:18]1[C:22](=[N:23][CH:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)Cl)[CH:21]=[C:20]([C:32]#[N:33])[NH:19]1.O>C(OCC)(=O)C>[Cl:17][C:9]1[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=[C:7]([Cl:6])[C:8]=1[N:18]1[C:22]([NH:23][CH2:24][C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:20]([C:32]#[N:33])=[N:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 178510205HCID 178510205, compound

Product 1

HCID 112007821-(2,6-Dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylmethylamino)pyrazole-3-carbonitrileYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To an ethanol (2 ml) suspension of 85 mg (2.2 mmol) of sodium borohydride was gradually added 0.5 g (1.1 mmol) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylchloromethylimino)pyrazole-3-carbonitrile at 20° C. or less. After 1 hour of stirring at room temperature, the mixture was gradually poured into 40 ml of water to precipitate crystals. After 30 minutes of stirring, the crystals were filtrated and washed with water until the pH of the filtrate became 6. The crystals thus obtained were dissolved in ethyl acetate and the solution was extracted after the addition of saturated saline. The organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated. The resulting crystals were filtrated, washed with a small amount of hexane and ethyl acetate, and dried to obtain 0.42 g (yield 92%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylmethylamino)pyrazole-3-carbonitrile.

Workup

  1. customat 20° C. or less
  2. customto precipitate crystals
  3. stirringAfter 30 minutes of stirring
  4. filtrationthe crystals were filtrated
  5. washwashed with water until the pH of the filtrate
  6. customThe crystals thus obtained
  7. extractionthe solution was extracted
  8. additionafter the addition of saturated saline
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltrated
  11. concentrationconcentrated
  12. filtrationThe resulting crystals were filtrated
  13. washwashed with a small amount of hexane and ethyl acetate
  14. customdried

Sources & evidence

ORD record
ord-db2bf85eb63c4acfa9854fc007a96251
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849633B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes