Hydrochloric Acid → N-[5-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]-5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonamide

HRID 252714Notes

Reaction equation

HRID 252714 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13]C(=O)C)=[N:10][C:9]=2[CH3:17])=[CH:4][C:3]=1[NH:18][S:19]([C:22]1[C:23]([CH3:29])=[N:24][N:25]([CH3:28])[C:26]=1[Cl:27])(=[O:21])=[O:20].Cl>C(O)C>[NH2:13][C:11]1[S:12][C:8]([C:5]2[CH:4]=[C:3]([NH:18][S:19]([C:22]3[C:23]([CH3:29])=[N:24][N:25]([CH3:28])[C:26]=3[Cl:27])(=[O:20])=[O:21])[C:2]([Cl:1])=[N:7][CH:6]=2)=[C:9]([CH3:17])[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11605316N-{5-[6-chloro-5-(5-chloro-1,3-dimethyl-1H-pyrazol-4-ylsulfonamido)pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide

Product 1

HCID 86620391N-[5-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]-5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonamideYield 36.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-{5-[6-chloro-5-(5-chloro-1,3-dimethyl-1H-pyrazol-4-ylsulfonamido)pyridin-3-yl]-4-methyl-1,3-thiazol-2-yl}acetamide (300 mg), a 6N aqueous hydrochloric acid solution (5 mL) and ethanol (5 mL) was stirred and heated to 80° C. for 5 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC. There was thus obtained the title compound as a white solid (100 mg); 1H NMR Spectrum: (DMSOd6) 2.19 (s, 6H), 3.73 (s, 3H), 7.39 (br s, 2H), 7.66 (s, 1H), 8.25 (s, 1H); Mass Spectrum: M+H+ 433.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated by evaporation
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a6644ff4454043b6a106379a87245a85
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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