5-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid → 4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-N-(2-hydroxy-ethyl)-benzenesulfonamide

HRID 1685759Notes

Reaction equation

HRID 1685759 reaction equation
[OH:1][NH:2][C:3](=[NH:17])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:16])(=[O:15])[NH:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1.[CH2:18]([N:20]([CH2:23][C:24]1[S:28][C:27]([C:29](O)=O)=[CH:26][C:25]=1[CH3:32])[CH2:21][CH3:22])[CH3:19]>>[CH2:18]([N:20]([CH2:23][C:24]1[S:28][C:27]([C:29]2[O:1][N:2]=[C:3]([C:4]3[CH:9]=[CH:8][C:7]([S:10]([NH:11][CH2:12][CH2:13][OH:14])(=[O:16])=[O:15])=[CH:6][CH:5]=3)[N:17]=2)=[CH:26][C:25]=1[CH3:32])[CH2:21][CH3:22])[CH3:19]

Participants

3

Reactant 2

HCID 672654805-Diethylaminomethyl-4-methyl-thiophene-2-carboxylic acidHCID 178513366HCID 178513366, compound

Product 1

HCID 672654514-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-N-(2-hydroxy-ethyl)-benzenesulfonamideYield 9.1%

Procedure

Starting from N-hydroxy-4-(2-hydroxy-ethylsulfamoyl)-benzamidine (201 mg, 0.774 mmol) and 5-diethylaminomethyl-4-methyl-thiophene-2-carboxylic acid (160 mg, 0.704 mmol), the title compound (29 mg) is obtained as a yellow oil according to Method A; LC-MS: tR=0.49 min; [M+1]+=451.02; 1H NMR (CDCl3): δ1.27 (t, J=7.3 Hz, 6H), 2.34 (s, 3H), 2.91 (q, J=7.3 Hz, 4H), 3.17-3.22 (m, 2H), 3.73-3.77 (m, 2H), 4.11 (s, 2H), 7.74 (s, 1H), 8.01-8.04 (m, 2H), 8.24 (s br, 1H), 8.30-8.33 (m, 2H).

Sources & evidence

ORD record
ord-bfe85e082f7247a0be1cf94edadf3f33
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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