3-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide → 3-(4-Aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

HRID 871008Notes

Reaction equation

HRID 871008 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([NH:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])=[O:20])[S:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].O1CCCC1.CN(C)C=O.CCOCC>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([NH:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C:22]3=[O:26])=[O:20])[S:12][N:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 1

HCID 716216273-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide

Product 1

HCID 716216283-(4-Aminophenyl)-5-{[(2-oxopyrrolidin-1-yl)carbonyl]amino}isothiazole-4-carboxamide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide (10.2 g,) and 10% palladium on carbon (2 g) in tetrahydrofuran (300 mL) and dimethylformamide (50 mL) was hydrogenated at 80 psi over 24 hr in metal bomb. The catalyst was removed by filtration through celite and washed with tetrahydrofuran. The filtrate was concentrated in vacuo to give an off white solid, which was stirred in ether (150 mL) and filtered to give the title compound as a off white solid (8.7 g, 94%).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an off white solid, which
  5. filtrationfiltered

Sources & evidence

ORD record
ord-36fa69814e094377b6cca9c4aa3d971b
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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