HCID 68880848, compound → HCID 57602517, compound

HRID 1787841Notes

Reaction equation

HRID 1787841 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:37])[CH2:16][NH:17][C:18]([CH3:36])([CH3:35])[CH2:19][CH2:20][N:21]2[C:25]([CH3:26])=[N:24][C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[N:22]2)=[CH:11][C:10]=1[CH2:38][OH:39])C1C=CC=CC=1>CO.[Pd]>[OH:37][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:38][OH:39])[CH:11]=1)[CH2:16][NH:17][C:18]([CH3:36])([CH3:35])[CH2:19][CH2:20][N:21]1[C:25]([CH3:26])=[N:24][C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)=[N:22]1

Participants

4

Reactant 1

HCID 68880848HCID 68880848, compound

Product 1

HCID 57602517HCID 57602517, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-{3-[3-(4-methoxy-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamino}-ethanol dissolved in 100 mL methanol are hydrogenated under normal pressure with 1 g of palladium on charcoal (5%) as catalyst. Then the catalyst is separated off and the filtrate is evaporated down. The residue is dissolved in 15 mL acetonitrile, acidified with 0.5 mL glacial acetic acid and seeded. The solid precipitated is filtered off and washed with acetonitrile and diethyl ether. Yield: 3.8 g (78%, acetate); m.p.=110-116° C.

Workup

  1. customThen the catalyst is separated off
  2. customthe filtrate is evaporated down
  3. dissolutionThe residue is dissolved in 15 mL acetonitrile
  4. customThe solid precipitated
  5. filtrationis filtered off
  6. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-d146b460d3904465aaaa50ff037c40c0
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

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