HCID 71621928, compound → HCID 71621929, compound

HRID 871026Notes

Reaction equation

HRID 871026 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]([NH:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:20])[S:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].O1CCCC1.CCOCC>[NH2:1][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]([NH:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:20])[S:12][N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 71621928HCID 71621928, compound

Product 1

HCID 71621929HCID 71621929, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-nitrophenyl)-5-({[(3-pyrrolidin-1-ylpropyl)amino]carbonyl}amino)isothiazole-4-carboxamide (16.0 g,) and 10% palladium on carbon (6 g) in tetrahydrofuran (1500 mL) was hydrogenated at 80 psi over 24 hr in metal bomb. Filter the catalyst on celite and washed with tetrahydrofuran. The filtrate was concentrated in vacuo to give off white solid, which was stirred in ether (200 mL) and filtered to give the title compound as a white solid (13.8 g, 93%).

Workup

  1. filtrationFilter the catalyst on celite
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give off white solid, which
  5. filtrationfiltered

Sources & evidence

ORD record
ord-de4c5c87707a47b9ba12a6f9b03da0eb
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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