Acetic Anhydride → HCID 178473836, compound

HRID 1486594Notes

Reaction equation

HRID 1486594 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[N:21]=[C:20]([NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[NH:19][N:18]=2)[CH:12]=[C:13]([Cl:15])[CH:14]=1.C(=O)(O)[O-].[Na+].C(OC(=O)C)(=O)C>C(#N)C>[Cl:15][C:13]1[CH:12]=[C:11]([NH:16][C:17]2[N:21]=[C:20]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:3](=[O:5])[CH3:2])[CH2:25][CH2:24]3)[NH:19][N:18]=2)[CH:10]=[C:9]([Cl:8])[CH:14]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178478184HCID 178478184, compound

Product 1

HCID 178473836HCID 178473836, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of N3-(3,5-dichlorophenyl)-N5-(piperidin-4-yl)-1H-1,2,4-triazole-3,5-diamine 2,2,2-trifluoroacetate (50 mg, 0.113 mmol) in acetonitrile (5 mL), was added saturated sodium bicarbonate solution (5 mL) and acetic anhydride (14 mg, 0.136 mmol). The reaction mixture was stirred overnight at rt. The solution was extracted with EtOAc (3×10 mL) and dried with sodium sulfate. Removal of solvent gave the crude product, which was purified by flash chromatography to give 35 mg (84%) desired product as a white solid. MS +m/z: 369.0 (M+H)+

Workup

  1. extractionThe solution was extracted with EtOAc (3×10 mL)
  2. dry with materialdried with sodium sulfate
  3. customRemoval of solvent
  4. customgave the crude product, which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3a2caf15307d4b4381b6663471d222b8
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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