(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide → (4R)-N-{3-[4-(3-Aminophenyl)-1-piperidinyl]propyl}-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

HRID 2085440Notes

Reaction equation

HRID 2085440 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:14]([C:15]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH:25]=[C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-])=O)[CH:28]=4)[CH2:23][CH2:22]3)=[O:16])=[C:13]([CH2:36][O:37][CH3:38])[NH:12][C:11](=[O:39])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]>C(O)C.[Pd]>[NH2:33][C:29]1[CH:28]=[C:27]([CH:24]2[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][CH2:18][NH:17][C:15]([C:14]3[C@@H:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=4)[NH:10][C:11](=[O:39])[NH:12][C:13]=3[CH2:36][O:37][CH3:38])=[O:16])[CH2:22][CH2:23]2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 69875018(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

Product 1

HCID 69875603(4R)-N-{3-[4-(3-Aminophenyl)-1-piperidinyl]propyl}-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide, 10% Pd/C in ethanol was hydrogenated (balloon method) for 2 days. The reaction mixture was filtered through Celite 545, washed with ethanol and concentrated to give the desired product.

Workup

  1. customfor 2 days
  2. filtrationThe reaction mixture was filtered through Celite 545
  3. washwashed with ethanol
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d651abcc5dec442a96835f5af7fc61dd
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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