N-(4-methyl-5-sulfamoylthiazol-2-yl)acetamide → 2-Amino-4-methyl-1,3-thiazole-5-sulfonamide

HRID 2388808Notes

Reaction equation

HRID 2388808 reaction equation
[NH2:1][S:2]([C:5]1[S:9][C:8]([NH:10]C(=O)C)=[N:7][C:6]=1[CH3:14])(=[O:4])=[O:3].FC1C(F)=CC=CC=1CSC1N=C(NS(C2SC(NC(=O)C)=NC=2C)(=O)=O)C=C(OC)N=1>O.NN.O>[NH2:10][C:8]1[S:9][C:5]([S:2]([NH2:1])(=[O:4])=[O:3])=[C:6]([CH3:14])[N:7]=1

Participants

5

Reactant 2

HCID 3244062N-(4-methyl-5-sulfamoylthiazol-2-yl)acetamideHCID 59558795N-{5-[({2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl)amino)sulfonyl]-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 186932442-Amino-4-methyl-1,3-thiazole-5-sulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

A suspension of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]acetamide (the product from Example 53, step (0.44 g) in hydrazine hydrate (1.5 ml) was stirred at room temperature for 4 h. The mixture was diluted with H2O and extracted with EtOAc (×4). The combined organic extracts were dried (MgSO4), filtered and evaporated to give the subtitle compound as an off-white solid. Yield 0.23 g.

Workup

  1. extractionextracted with EtOAc (×4)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-30286492fffc497d981a09434d72f1e7
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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