Ammonia → 3-{5-[4-Methyl-5-(4-sulfamoyl-phenyl)-thiazol-2-ylamino]-[1,3,4]thiadiazol-2-yl}-propionic acid

HRID 908189Notes

Reaction equation

HRID 908189 reaction equation
[NH:1]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[N:7][N:6]=1)[C:2]([NH2:4])=[S:3].O=[C:16]([CH3:28])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1.N>>[CH3:28][C:16]1[N:4]=[C:2]([NH:1][C:5]2[S:9][C:8]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[N:7][N:6]=2)[S:3][C:17]=1[C:18]1[CH:19]=[CH:20][C:21]([S:24](=[O:26])(=[O:25])[NH2:27])=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 215301384-(2-Oxopropyl)benzene-1-sulfonamideHCID 866062213-(5-Thioureido-[1,3,4]thiadiazol-2-yl)-propionic acid

Product 1

HCID 866062223-{5-[4-Methyl-5-(4-sulfamoyl-phenyl)-thiazol-2-ylamino]-[1,3,4]thiadiazol-2-yl}-propionic acid

Procedure

The titled compound is prepared from 3-(5-thioureido-[1,3,4]thiadiazol-2-yl)-propionic acid (56b) and from 4-(2-oxo-propyl)-benzenesulfonyl chloride (prepared as described in European patent specification EP 91749 A2) following procedures described for Example 1 using ammonia to prepare the sulfonamide.

Sources & evidence

ORD record
ord-4788d986175a43fe8f863eaa41a79975
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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