Acetic Anhydride → HCID 25255764, compound

HRID 1963016Notes

Reaction equation

HRID 1963016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][O:14][C:15]3[C:16]([F:26])=[C:17]([C:22]([F:25])=[CH:23][CH:24]=3)[C:18](=[N:20]O)[NH2:19])[S:10][N:9]=2)=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.C1COCC1>CC(O)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13][O:14][C:15]3[C:16]([F:26])=[C:17]([C:22]([F:25])=[CH:23][CH:24]=3)[C:18](=[NH:19])[NH2:20])[S:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 74430595HCID 74430595, compound

Product 1

HCID 25255764HCID 25255764, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-((3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl)methoxy)-2,6-difluoro-N′-hydroxybenzimidamide (0.02 g, 0.05 mmol) in AcOH (0.50 ml) was added acetic anhydride (6 μL, 0.06 mmol) followed by addition of THF (1.0 ml) under nitrogen atmosphere. The resulting reaction mixture was stirred at room temperature for 1 h after which Pd-C (10%, 2.0 mg) was added and the resulting solution was stirred under hydrogen for 4 h. After the completion of the reaction (TLC monitoring), the reaction mass was filtered through celite bed, washed the celite bed with THF (3-4 times) and concentrated the filtrate. The residue was purified over neutral alumina (40% MeOH-DCM) to get the desired product (11 mg (58%).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. customAfter the completion of the reaction (TLC monitoring)
  4. filtrationthe reaction mass was filtered through celite bed
  5. washwashed the celite bed with THF (3-4 times)
  6. concentrationconcentrated the filtrate
  7. customThe residue was purified over neutral alumina (40% MeOH-DCM)

Sources & evidence

ORD record
ord-9a2bcec18c7045318a38e38240b3b895
Source dataset
uspto-grants-2013_04
Patent number
US08415383B2

Reaction notes

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