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

HRID 851996Notes

Reaction equation

HRID 851996 reaction equation
[CH3:1][O:2][CH2:3][C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH2:38][C:39]2[CH:48]=[CH:47][C:42]([C:43]([NH:45]O)=[NH:44])=[CH:41][CH:40]=2)[CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][NH:32][C:31]2=[O:37])(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>CN(C)C=O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]3[N:44]=[C:4]([CH2:3][O:2][CH3:1])[O:6][N:45]=3)=[CH:47][CH:48]=2)[CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][NH:32][C:31]2=[O:37])(=[O:27])=[O:28])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12251Methoxyacetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 178513311HCID 178513311, compound

Product 1

HCID 694916874-chloro-N-[4-(5-methoxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methoxyacetic acid (86 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 0.46 g (90%) 4-chloro-N-[4-(5-methoxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=505.0 (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-a082fd40fc024a099dbdc6e47ac2fb1d
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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