Acetic Acid → 4-chloro-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 851997Notes

Reaction equation

HRID 851997 reaction equation
[C:1]([OH:4])(=O)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]([CH2:36][C:37]2[CH:46]=[CH:45][C:40]([C:41]([NH:43]O)=[NH:42])=[CH:39][CH:38]=2)[CH:28]2[CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:29]2=[O:35])(=[O:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:27]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([C:41]3[N:42]=[C:1]([CH3:2])[O:4][N:43]=3)=[CH:45][CH:46]=2)[CH:28]2[CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:29]2=[O:35])(=[O:25])=[O:26])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 178513311HCID 178513311, compound

Product 1

HCID 694920034-chloro-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetic acid (63 μl, 1.10 mmol) in 5 ml dimethylformamide were added 1,1′-carbonyl-diimidazole (0.18 g, 1.10 mmol). The mixture was stirred at room temperature for 10 minutes, heated to 40° C. for a few minutes and cooled to room temperature. 4-{[(4-Chloro-benzenesulfonyl)-(2-oxo-azepan-3-yl)-amino]-methyl}-N-hydroxy-benzamidine (0.45 g, 1.00 mmol) was added and the mixture was stirred at 100° C. for 5 hours and then poured into water. Filtration and chromatography on silicagel with ethylacetate/heptane (1/1 to 4/1) yielded 0.43 g (91%) 4-chloro-N-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=474.9 (MH+, 100).

Workup

  1. temperatureheated to 40° C. for a few minutes
  2. temperaturecooled to room temperature
  3. stirringthe mixture was stirred at 100° C. for 5 hours
  4. filtrationFiltration and chromatography on silicagel with ethylacetate/heptane (1/1 to 4/1)

Sources & evidence

ORD record
ord-b86cf2568d1243c48e79c93007ddbd18
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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