HCID 70357434, compound → HCID 19864527, compound

HRID 1199984Notes

Reaction equation

HRID 1199984 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[C:20]([C:21](=[O:29])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[C:19]([CH3:30])[NH:18][C:17]([CH3:31])=[C:16]1[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][N:39]1[C:43]([CH3:44])=[N:42][N:41]=[C:40]1[CH3:45])=[O:33])C1C=CC=CC=1>C(O)C.[Pd]>[OH2:8].[CH3:31][C:17]1[NH:18][C:19]([CH3:30])=[C:20]([C:21](=[O:29])[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[OH:8])[C:16]=1[C:32]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][N:39]1[C:40]([CH3:45])=[N:41][N:42]=[C:43]1[CH3:44])=[O:33]

Participants

4

Reactant 1

HCID 70357434HCID 70357434, compound

Product 1

HCID 19864527HCID 19864527, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-Benzyloxyphenyl)-2,6-dimethyl-3-[4-(3,5-dimethyl-1,2,4-triazol-4yl)butoxycarbonyl]-5-(N-pyrid-2-ylcarbamoyl)-1,4-dihydropyridine (0.3 g--see Example 11) was dissolved in ethanol (10 ml) containing 10% palladium-on-charcoal and the mixture was hydrogenated at room temperature under pressure (30 p.s.i.=206.8 kPa) for 4 hours. The catalyst was filtered off and the filtrate evaporated under vacuum. The residue was then chromatographed on silica gel eluting with EtOAc containing 15% Et2NH and the fractions containing the product were combined and evaporated to give the title compound, (0.12 g, 47%), m.p. 125°-135°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was then chromatographed on silica gel eluting with EtOAc containing 15% Et2NH
  4. additionthe fractions containing the product
  5. customevaporated

Sources & evidence

ORD record
ord-39fa333a581e483fac2beae5b28a2c32
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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