HCID 54542548, compound → HCID 54343124, compound

HRID 1934704Notes

Reaction equation

HRID 1934704 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:7][C:8]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[O:11])[CH3:6])=[N+]=[N-]>C(O)C.ClCCl.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:7][C:8]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[O:11])[CH3:6]

Participants

5

Reactant 1

HCID 54542548HCID 54542548, compound

Product 1

HCID 54343124HCID 54343124, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(2-azido-1-methylethylamino)-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (505 mg) in a mixture of ethanol (5 mL) and dichloromethane (3 mL) was added 10% palladium on activated carbon (60 mg), and the mixture was stirred under hydrogen atmosphere (1 atm) for 3 hours at ambient temperature. The resulting mixture was filtered through celite and washed with ethanol. The filtrate and the washings were combined and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with 10% methanol in chloroform to give (S)-2-(2-amino-1-methylethylamino)-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (393 mg) as a solid substance.

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashed with ethanol
  3. customevaporated in vacuo
  4. washeluting with 10% methanol in chloroform

Sources & evidence

ORD record
ord-eea7c9308e1f46de94fdf51f3be6af45
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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