Sodium borohydride → HCID 178478143, compound

HRID 1486568Notes

Reaction equation

HRID 1486568 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]([CH:23]=O)=[N:21][CH:22]=1.[BH4-].[Na+]>CO>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][NH:15][C:13]2[NH:12][N:11]=[C:10]([NH:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:14]=2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 101032675-Chloropyridine-2-carboxaldehydeHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178478143HCID 178478143, compoundYield 90%

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-formylpyridine (60 mg, 424 μmol) in MeOH (3 ml) was stirred at room temperature for one day and then 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 (163 mg, 4.3 mmol) was added in a few portions 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. Crystallization from DCM afforded a white solid as desired product (96.6 mg, 90% yield). MS +m/z: 369 (M+H)+

Workup

  1. customat 45° C. for two days to 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
  9. customCrystallization from DCM

Sources & evidence

ORD record
ord-d2f3481082064c819b77f23375b73b89
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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