Acetic Anhydride → 3-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamide

HRID 1619647Notes

Reaction equation

HRID 1619647 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[S:15][C@@H:16]([F:20])[C@H:17](O)[N:18]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[S:15][C:16]([F:20])=[CH:17][N:18]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 580423263-cyano-4-fluoro-N-[(4S,5R)-5-fluoro-4-hydroxy-4,5-dihydro-1,3-thiazol-2-yl]benzenesulfonamide

Product 1

HCID 580422733-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-cyano-4-fluoro-N-[(4S,5R)-5-fluoro-4-hydroxy-4,5-dihydro-1,3-thiazol-2-yl]benzenesulfonamide (Preparation 33, 1.42 g, 4.45 mmol) in dichloromethane (150 mL) was added triethylamine (6.20 mL, 44.5 mmol) and acetic anhydride (1.30 mL, 13.8 mL). The reaction mixture was stirred at room temperature under an atmosphere of nitrogen for 18 hours. The mixture was washed with a 2M aqueous solution of hydrogen chloride. The organics were separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting residue was triturated with dichloromethane to afford the title compound as a pale yellow solid (825 mg, 62%).

Workup

  1. washThe mixture was washed with a 2M aqueous solution of hydrogen chloride
  2. customThe organics were separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-f68c35a0f3e1464e8d3d20925f0c6118
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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