Acetic Acid → HCID 178449983, compound

HRID 1486578Notes

Reaction equation

HRID 1486578 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.[C:16]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][CH:25]=1)(=[O:23])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O)(=O)C.Cl>CO>[C:16]([NH:20][S:21]([C:24]1[CH:25]=[CH:26][C:27]([CH2:30][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)=[CH:28][CH:29]=1)(=[O:22])=[O:23])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazoleHCID 86063588HCID 86063588, compound

Product 1

HCID 178449983HCID 178449983, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (100 mg, 410 μmol) in MeOH (5 mL) was added N-tert-butyl-4-formylbenzenesulfonamide (109 mg, 451 μmol) followed by acetic acid (36.7 mg, 35 μl, 611 μmol). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (65.7 mg, 615 μmol) was added and the stirring was continued for 3 days. The reaction mixture was poured into 0.1N HCl solution (25 ml) and was extracted with EtOAc (3×30 ml). The combined organic solution was washed with brine, dried over Na2SO4 and concentrated to give a residue. The crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM) to give an off white solid as desired product (98 mg, 51% yield). MS +m/z: 469 (M+H)+

Workup

  1. addition2-picoline borane complex (65.7 mg, 615 μmol) was added
  2. waitthe stirring was continued for 3 days
  3. extractionwas extracted with EtOAc (3×30 ml)
  4. washThe combined organic solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-f5cc180b025a4f54a9ab50ad9b637699
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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