5-(3-(3-Methoxypropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide → 3-(4-Aminophenyl)-5-({[(3-methoxypropyl)amino]carbonyl}amino)isothiazole-4-carboxamide

HRID 870998Notes

Reaction equation

HRID 870998 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:26])[NH:8][C:9]1[S:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[C:10]=1[C:23]([NH2:25])=[O:24].[H][H]>CO.[Pt]=O>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[C:10]([C:23]([NH2:25])=[O:24])=[C:9]([NH:8][C:7]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:26])[S:13][N:12]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 716208355-(3-(3-Methoxypropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 716230313-(4-Aminophenyl)-5-({[(3-methoxypropyl)amino]carbonyl}amino)isothiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(3-(3-methoxypropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide (4 mg, 0.009 mmol) and catalytic platinum oxide in 4 mL MeOH was hydrogenated under 60 PSI hydrogen. After 17 hours, the mixture was filtered and rotary evaporated to a white solid. The solid was partitioned between EtOAc and aqueous NaHCO3 solution, the EtOAc layer dried with anhydrous Na2SO4 and evaporated to the title compound as a white solid (2 mg, 66%).

Workup

  1. filtrationthe mixture was filtered
  2. customrotary evaporated to a white solid
  3. customThe solid was partitioned between EtOAc and aqueous NaHCO3 solution
  4. dry with materialthe EtOAc layer dried with anhydrous Na2SO4
  5. customevaporated to the title compound as a white solid (2 mg, 66%)

Sources & evidence

ORD record
ord-f39bcd0e128342e8bac99c354390cea0
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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