Acetic Anhydride → HCID 71735082, compound

HRID 1051881Notes

Reaction equation

HRID 1051881 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH:8]12[CH2:13][CH:12]1[CH2:11][N:10]([C:14]([C:16]1[S:17][C:18]([C:28]3[CH:33]=[CH:32][C:31]([S:34]([NH2:37])(=[O:36])=[O:35])=[CH:30][CH:29]=3)=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:20]=1)=[O:15])[CH2:9]2>N1C=CC=CC=1.O>[CH:12]12[CH2:13][CH:8]1[CH2:9][N:10]([C:14]([C:16]1[S:17][C:18]([C:28]3[CH:33]=[CH:32][C:31]([S:34]([NH:37][C:5](=[O:7])[CH3:6])(=[O:36])=[O:35])=[CH:30][CH:29]=3)=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[N:20]=1)=[O:15])[CH2:11]2

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 71737164HCID 71737164, compound2×

Product 1

HCID 71735082HCID 71735082, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.66 g, 0.65 mmol) was added to stirred solution of 44243-azabicyclo[3.1.0]hexane-3-carbonyl)-4-(4-chlorophenyl)thiazol-5-yl)benzenesulfonamide (Compound 73, 0.3 g, 0.65 mmol) in pyridine (5 ml) at 0° C. The reaction mixture was stirred at room temperature for 2 hr. The progress of reaction was monitored by TLC. The reaction mixture was diluted with water (25 ml) and extracted with ethyl acetate (2×25 ml). The combined organic layer was dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 25% ethyl acetate in hexanes as an eluent to obtain the title compound (0.07 g, 21.4%). MS: m/z 502 (M+1).

Workup

  1. customThe progress of reaction
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. dry with materialThe combined organic layer was dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a crude product
  6. customwhich was purified by flash column chromatography

Sources & evidence

ORD record
ord-13b8aed74cfe49e48367e9d6264e6185
Source dataset
uspto-grants-2016_07
Patent number
US09388196B2

Reaction notes

Loading…