HCID 118006473, compound → HCID 118005957, compound

HRID 1484715Notes

Reaction equation

HRID 1484715 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([C:29]3[N:30]=[C:31]([NH:34][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)[S:32][CH:33]=3)=[C:24]([CH3:43])[CH:23]=2)[CH2:18][CH2:17]1)=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([C:29]3[N:30]=[C:31]([NH:34][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)[S:32][CH:33]=3)=[C:24]([CH3:43])[CH:23]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 118006473HCID 118006473, compound

Product 1

HCID 118005957HCID 118005957, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(4-(4-(4-(2-(2-(2-(2-azidoethoxyl)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (4.7 mg, 0.0077 mmol) in EtOH (1 mL) was added Pd/C (10% Pd, 3 mg). The mixture was hydrogenated overnight at room temperature under 1 atm H2 pressure. The mixture was then filtered through a pad of celite and concentrated to give N-(4-(4-(4-(2-(2-(2-(2-amino ethoxy)ethoxy)ethoxy)ethoxy)piperidin-1-yl)-2,6-dimethylphenyl)thiazol-2-yl)isonicotinamide (1.1 mg, yield 24.5%), which was used directly without further purification.

Workup

  1. filtrationThe mixture was then filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5386156ce2bd4ae899d3aa6b602fcc79
Source dataset
uspto-grants-2016_08
Patent number
US09422275B2

Reaction notes

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