[1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester → [2-(3-ethyl-indazol-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896370Notes

Reaction equation

HRID 896370 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[CH:34]=[CH:33][C:12]2[N:13]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:14]([CH2:16][N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([CH:26]=[CH2:27])=[N:18]3)=[N:15][C:11]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[CH:34]=[CH:33][C:12]2[N:13]([CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[C:14]([CH2:16][N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:19]([CH2:26][CH3:27])=[N:18]3)=[N:15][C:11]=2[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 69719540[1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 69718284[2-(3-ethyl-indazol-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl esterYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [1-(4-hydroxy-butyl)-2-(3-vinyl-indazol-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (115 mg, 0.24 mmol) in methanol (35 mL) was added 10% Pd/C (12 mg) and this suspension was rocked in a Parr shaker under a hydrogen atmosphere (45 psi) for 2 hrs. The catalyst was removed by filtration and the filtrate concentrated in vacuo to yield [2-(3-ethyl-indazol-1-ylmethyl)-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (106 mg, 92%) as a white foam:

Workup

  1. customfor 2 hrs
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-37f690998bae45b688a086e416a0b792
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

Loading…