Hydrochloric Acid → HCID 67131662, compound

HRID 1591655Notes

Reaction equation

HRID 1591655 reaction equation
C(OC([NH:11][C:12](=[NH:37])[C:13]1[CH:36]=[CH:35][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:23](=[O:33])[C:22]2=[O:34])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.[ClH:38]>CN(C)C=O.[C].[Pd]>[ClH:38].[NH2:37][C:12](=[NH:11])[C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:23](=[O:33])[C:22]2=[O:34])=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 145783719HCID 145783719, compound

Product 1

HCID 67131662HCID 67131662, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent2×

Procedure

1.74 g of methyl 3-[4-(3-{4-[{[(benzyloxy)carbonyl]amino}(imino)methyl]phenoxy}propyl)-2,3-dioxo-1-piperazinyl]propanoate was dissolved in 10 ml of N,N-dimethylformamide. Thereafter, 0.52 g of 5% palladium-carbon suspended in 7.4 ml of N,N-dimethylformamide and 0.85 ml of 6 mol/L hydrochloric acid were added to the solution, followed by stirring under a hydrogen atmosphere at room temperature under atmospheric pressure for 2 hours. After completion of the reaction, the catalyst was removed by filtration, and the residue was washed with 20 ml of N,N-dimethylformamide. The filtrate was then concentrated under a reduced pressure. 20 ml of xylene was added to the obtained residue, and the mixture was further concentrated under a reduced pressure to obtain 1.37 g of methyl 3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-2,3-dioxo-1-piperazinyl]propanoate hydrochloride.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration
  3. washthe residue was washed with 20 ml of N,N-dimethylformamide
  4. concentrationThe filtrate was then concentrated under a reduced pressure
  5. addition20 ml of xylene was added to the obtained residue
  6. concentrationthe mixture was further concentrated under a reduced pressure

Sources & evidence

ORD record
ord-20edeb6147e64f63a850fd879760d180
Source dataset
uspto-grants-2007_11
Patent number
US07291617B2

Reaction notes

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