Hydrochloric Acid → {4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid

HRID 1685760Notes

Reaction equation

HRID 1685760 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[NH:19])[NH:17][OH:18])=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32](O)=O)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22].Cl>[Li+].[OH-].CO>[CH2:21]([N:23]([CH2:26][C:27]1[S:31][C:30]([C:32]2[O:18][N:17]=[C:16]([C:13]3[CH:12]=[CH:11][C:10]([S:7]([NH:6][CH2:5][C:4]([OH:3])=[O:20])(=[O:8])=[O:9])=[CH:15][CH:14]=3)[N:19]=2)=[CH:29][C:28]=1[CH3:35])[CH2:24][CH3:25])[CH3:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178472928HCID 178472928, compound

Product 1

HCID 67265676{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acidYield 1.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzenesulfonylamino}-acetic acid ethyl ester (98 mg) is obtained starting from [4-(N-hydroxycarbamimidoyl)-benzenesulfonylamino]-acetic acid ethyl ester (233 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol) according to Method A; LC-MS: tR=0.57 min; [M+1]+=493.17. This material (98 mg, 199 μmol) is dissolved in 2 N aq. LiOH (25 mL) and methanol (25 mL). The mixture is stirred at rt for 20 h before it is acidified by adding 1 N aq. HCl and extracted twice with EA. The combined organic extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (6 mg) as a white solid; LC-MS: tR=0.50 min; [M+1]+=465.02.

Workup

  1. extractionextracted twice with EA
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-c0d9b36298bd4f348e8a9beccd73de7c
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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