Acetic Anhydride → N-(1-(5-bromothiazol-2-yl)cyclobutylsulfonyl)acetamide

HRID 1040088Notes

Reaction equation

HRID 1040088 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)=[N:4][CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([C:7]2([S:11]([NH:14][C:15](=[O:17])[CH3:16])(=[O:13])=[O:12])[CH2:8][CH2:9][CH2:10]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 674322841-(5-Bromothiazol-2-yl)cyclobutane-1-sulfonamide

Product 1

HCID 67430287N-(1-(5-bromothiazol-2-yl)cyclobutylsulfonyl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

1-(5-Bromo-1,3-thiazol-2-yl)cyclobutanesulfonamide (110 mg, 0.370 mmol, prepared according to Example 70, Steps 1-5) was taken up in pyridine (5 mL), and acetic anhydride (524 μL, 5.55 mmol) was added. The reaction was stirred at 70° C. overnight. The reaction was concentrated to dryness, diluted with water, acidified with 2 N HCl, and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated to give N-{[1-(5-bromo-1,3-thiazol-2-yl)cyclobutyl]sulfonyl}acetamide (120 mg, 96%) as a beige solid. MS ESI: [M+H]+ 338.9/340.9.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2 (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5cb2022c662d4356bc10894628d1e27b
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

Loading…