HCID 15698062, compound → HCID 14697223, compound

HRID 847059Notes

Reaction equation

HRID 847059 reaction equation
[N:1]([CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([O:25][CH3:26])=[O:24])=[CH:13][CH:12]=2)[C:8]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:7][C:6]=1[Cl:31])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:16]=2)[C:8]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:7][C:6]=1[Cl:31]

Participants

4

Reactant 1

HCID 15698062HCID 15698062, compound

Product 1

HCID 14697223HCID 14697223, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Azidomethyl-2-butyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloroimidazole (3.48 g) was hydrogenated at 1 atm in methanol (100 mL) over 10% palladium/carbon (0.5 g). After 1 hour, the mixture was filtered through Celite® and the solvent removed in vacuo to give product (2.80 g) as an oil. NMR (200 MHz, CDCl3) δ7.84 (d, 1H, J=7 Hz); 7.52 (t, 1H, J=7 Hz); 7.40 (t, 1H, J=7 Hz); 7.30 (d, 1H, J=7 Hz); 7.26 (d, 2H, J=8 Hz); 7.02 (d, 2H, J=8 Hz); 5.27 (s, 2H); 3.74 (s, 2H); 3.65 (s, 3H); 2.60 (t, 2H, J=7 Hz); 1.67 (t of t, 2H, J=7,7Hz); 1.36 (t of q, 2H, J=7,7 Hz); 0.86 (t, 3H, J=7 Hz). Anal. Calcd. for C23H26ClN3O2.(DMSO)0.5 : C, 63.91; H, 6.48; N, 9.32. Found: C, 63.78; H, 6.30; N, 9.14.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-43303881fe3442f2a8766ee54b455434
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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