HCID 71621784, compound → HCID 71621785, compound

HRID 871015Notes

Reaction equation

HRID 871015 reaction equation
[C:1]([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]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:13]=1[C:26]([NH2:28])=[O:27])=[O:10])(=[O:3])[CH3:2]>[Pd].O1CCCC1.CN(C)C=O.CCOCC>[C:1]([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:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)[C:13]=1[C:26]([NH2:28])=[O:27])=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 1

HCID 71621784HCID 71621784, compound

Product 1

HCID 71621785HCID 71621785, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[({[4-(aminocarbonyl)-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]propyl acetate (12.0 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. 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 (100 mL) and filtered gave the title compound as an off white solid (8.5 g, 77%).

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-de990d76413c4d1290b8111b048cd9f8
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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