HCID 86689231, compound → HCID 71621925, compound

HRID 871022Notes

Reaction equation

HRID 871022 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=[O:14])[CH:8]=2)[C:3]=1[C:16]([NH2:18])=[O:17].[H][H]>CO.[Pt]=O>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][OH:14])[CH:8]=2)[C:3]=1[C:16]([NH2:18])=[O:17]

Participants

5

Reactant 2

HCID 86689231HCID 86689231, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71621925HCID 71621925, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)Catalyst2×HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-(3-nitrophenyl)isothiazole-4-carboxamide (50 mg, 0.19 mmol) and platinum oxide (20 mg, 0.088 mmol) in 5 mL MeOH was hydrogenated under 60 PSI hydrogen. After 5 hours an additional catalytic amount of platinum oxide was added and the reaction continued for 67 hours. The reaction mixture was filtered using Celite and the filter bed rinsed with 40% MeOH/CHCl3. The filtrate was evaporated to give 32 mg of yellow solid. Then 22 mg of this material was chromatographed eluting with CHCl3/MeOH to give the title compound as a pale yellow solid (10.2 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter bed rinsed with 40% MeOH/CHCl3
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b6951dc5e0bc420f9bf66f7455cb855c
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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