HCID 68879849, compound → HCID 57602519, compound

HRID 1787844Notes

Reaction equation

HRID 1787844 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:36])[CH2:16][NH:17][C:18]([CH3:35])([CH3:34])[CH2:19][CH2:20][N:21]2[CH:25]=[N:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)=[N:22]2)=[CH:11][C:10]=1[CH2:37][OH:38])C1C=CC=CC=1>[Pd].CO.O1CCCC1>[OH:36][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:37][OH:38])[CH:11]=1)[CH2:16][NH:17][C:18]([CH3:35])([CH3:34])[CH2:19][CH2:20][N:21]1[CH:25]=[N:24][C:23]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[N:22]1

Participants

5

Reactant 1

HCID 68879849HCID 68879849, compound

Product 1

HCID 57602519HCID 57602519, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.8 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-{3-[3-(4-methoxy-phenyl)-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamino}-ethanol are hydrogenated with 0.6 g of palladium on charcoal (5%) as catalyst in 75 mL methanol and 75 mL tetrahydrofuran. Then the catalyst is suction filtered and the filtrate is evaporated down. The residue is dissolved in 15 mL 15% m acetonitrile, acidified with formic acid and combined with a crystallisation aid. The precipitated product is separated off and washed. Yield: 2.8 g (81%, formate); m.p.=142-145° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. dissolutionThe residue is dissolved in 15 mL 15% m acetonitrile
  4. customThe precipitated product is separated off
  5. washwashed

Sources & evidence

ORD record
ord-f03ed9c7507f4091b2c9ef9cde7be8c9
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

Loading…