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

HRID 851998Notes

Reaction equation

HRID 851998 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([N:35]([CH2:44][C:45]2[CH:54]=[CH:53][C:48]([C:49]([NH:51]O)=[NH:50])=[CH:47][CH:46]=2)[CH:36]2[CH2:42][CH2:41][CH2:40][CH2:39][NH:38][C:37]2=[O:43])(=[O:34])=[O:33])=[CH:28][CH:27]=1.O>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[O:12][N:50]=[C:49]([C:48]2[CH:53]=[CH:54][C:45]([CH2:44][N:35]([CH:36]3[CH2:42][CH2:41][CH2:40][CH2:39][NH:38][C:37]3=[O:43])[S:32]([C:29]3[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=3)(=[O:34])=[O:33])=[CH:46][CH:47]=2)[N:51]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 290301(Benzyloxy)acetic acidHCID 178513311HCID 178513311, compound

Product 1

HCID 69491001N-[4-(5-benzyloxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-4-chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamideYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyloxyacetic acid (162 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 0.51 g (87%) N-[4-(5-benzyloxymethyl-[1,2,4]oxadiazol-3-yl)-benzyl]-4-chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide as white solid, MS: m/e (%)=581.1 (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-b645750a0cc84dfca460f90462d97c8b
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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