Sodium borohydride → HCID 178506170, compound

HRID 1486567Notes

Reaction equation

HRID 1486567 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]([F:28])([F:27])[F:26])=[C:21]([CH:24]=1)[CH:22]=O.[BH4-].[Na+]>CO>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]([F:26])([F:27])[F:28])=[C:21]([CH:24]=1)[CH2:22][NH:15][C:13]1[NH:12][N:11]=[C:10]([NH:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:14]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 177507585-Chloro-2-(trifluoromethyl)benzaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178506170HCID 178506170, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (70 mg, 287 μmol) and 5-chloro-2-(trifluoromethyl)benzaldehyde (85 mg, 408 μmol) in MeOH (3 ml) was stirred at 45° C. for two days to give a suspension, cooled to −20° C. and was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in EtOAc (5 ml) and washed with water (2×4 ml), dried over MgSO4 and concentrated. Trituration with hexanes afforded a white solid as desired product (88 mg, 70% yield). MS +m/z: 436 (M+H)+

Workup

  1. customto give a suspension
  2. filtrationwas filtered
  3. customto collect the solid
  4. customThe solvent was removed
  5. dissolutionthe reaction mixture was redissolved in EtOAc (5 ml)
  6. washwashed with water (2×4 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4b3e8a32fd3843ca92eb820fa4091687
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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