5-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide → 3-(4-Aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamide

HRID 870993Notes

Reaction equation

HRID 870993 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:30])[NH:12][C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[C:14]=2[C:27]([NH2:29])=[O:28])[CH2:3][CH2:2]1.[H][H]>CO.[Pt]=O>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:15]2[C:14]([C:27]([NH2:29])=[O:28])=[C:13]([NH:12][C:11]([NH:10][CH2:9][CH2:8][CH2:7][N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[O:30])[S:17][N:16]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 716230305-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 716213173-(4-Aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamideYield 46.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(3-(3-morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide (110 mg, 0.25 mmol) and platinum oxide (25 mg, 0.11 mmol) in 15 mL MeOH was hydrogenated under 60 PSI hydrogen. After 16.5 hours, the mixture was filtered and rotary evaporated to an off-white solid. Then an additional 16 mg of impure product from another reaction was combined and this material chromatographed eluting with gradient 5% to 15% MeOH in CHCl3 to give the title compound as an off-white solid (47 mg, 40%).

Workup

  1. filtrationthe mixture was filtered
  2. customrotary evaporated to an off-white solid
  3. customthis material chromatographed
  4. washeluting with gradient 5% to 15% MeOH in CHCl3

Sources & evidence

ORD record
ord-0937739898c14f4c9bcb02d9eb014ce0
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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