HCID 22130341, compound → 1H-Imidazole-2-methanamine, 5-((3,5-dichlorophenyl)methyl)-1-methyl-4-(1-methylethyl)-

HRID 1857736Notes

Reaction equation

HRID 1857736 reaction equation
[N:1]([CH2:4][C:5]1[N:6]([CH3:22])[C:7]([CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)=[N+]=[N-].[H][H]>C(O)C.[C].[Pd]>[NH2:1][CH2:4][C:5]1[N:6]([CH3:22])[C:7]([CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1

Participants

5

Reactant 2

HCID 22130341HCID 22130341, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 4740131H-Imidazole-2-methanamine, 5-((3,5-dichlorophenyl)methyl)-1-methyl-4-(1-methylethyl)-Yield 68.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 8 ml of ethanol was dissolved 150 mg (0.44 mmol) of 2-azidomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (60), and 50 mg of 10% palladium carbon was added at -20° C. The mixture was stirred at room temperature under a stream of hydrogen. After 4 hours, the reaction mixture was filtered through Celite, and the filtrate was concentrated to give 94 mg of Compound I-101 (yield 68%).

Workup

  1. additionwas added at -20° C
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2606da91e10c4e23a10576203b2c0e77
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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