HCID 71621785, compound → HCID 86689230, compound

HRID 871016Notes

Reaction equation

HRID 871016 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([NH:11][C:12]1[S:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[C:13]=1[C:24]([NH2:26])=[O:25])=[O:10])(=O)C>[Pd].O1CCCC1.CN(C)C=O.CCOCC>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[C:13]([C:24]([NH2:26])=[O:25])=[C:12]([NH:11][C:9]([NH:8][CH2:7][CH2:6][CH2:5][OH:4])=[O:10])[S:16][N:15]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 1

HCID 71621785HCID 71621785, compound

Product 1

HCID 86689230HCID 86689230, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[({[4-(aminocarbonyl)-3-(4-aminophenyl)isothiazol-5-yl]amino}carbonyl)amino]propyl acetate (10.0 g) and 10% palladium on carbon (3 g) in tetrahydrofuran (400 mL) and dimethylformamide (100 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 a yellow solid, which was stirred in ether (100 mL) and collected by filtration to give the title compound as a light yellow solid (8.8 g, 96%).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a yellow solid, which
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-07fd595e8ebb4fb4ac3a256d8f65b9c3
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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