Ammonium Chloride → HCID 178470830, compound

HRID 1738694Notes

Reaction equation

HRID 1738694 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[S:7][C:8]([CH2:10][CH:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][NH:28][C:27](=[N:30]C(OCC5C=CC([N+]([O-])=O)=CC=5)=O)[NH:26][CH2:25]4)=[CH:19][CH:18]=3)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:5]=2[CH:4]=1)#[N:2].[Cl-:46].[NH4+]>C(O)C.[C].[Pd]>[ClH:46].[C:1]([C:3]1[CH:45]=[CH:44][C:6]2[S:7][C:8]([CH2:10][CH:11]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH:24]4[CH2:25][NH:26][C:27](=[NH:30])[NH:28][CH2:29]4)=[CH:21][CH:22]=3)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 178470829HCID 178470829, compound

Product 1

HCID 178470830HCID 178470830, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 100 ml portion of ethanol was dissolved 1.5 g of ethyl 3-(5-cyanobenzo[b]thien-2-yl)-2-[4-[[2-(p-nitrobenzyloxycarbonylimino)hexahydropyrimidin-5-yl]oxy]phenyl]propionate obtained in the above step c). To the thus prepared solution were added 0.5 g of ammonium chloride and 0.5 g of 10% palladium carbon catalyst (50% wet type). The resulting mixture was subjected to 2 hours of catalytic hydrogenation under normal pressure. After removing the catalyst by filtration and distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a chloroform/ethanol mixture as an elution solvent, thereby obtaining 1.0 g of the title compound.

Workup

  1. customobtained in the above step c)
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. distillationdistilling off the solvent
  5. customthe resulting residue was purified

Sources & evidence

ORD record
ord-37dd961032ad43f79c0e8a730d0ac35b
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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