HCID 20255099, compound → HCID 20255197, compound

HRID 638041Notes

Reaction equation

HRID 638041 reaction equation
C([N:8]([CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40](=[O:42])[NH2:41])[CH:34]=1)[CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([CH3:24])[C:22]([C:25]([F:28])([F:27])[F:26])=[N:21][N:20]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>[Pd].CO>[C:40]([C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][C:36]=1[OH:39])[O:32][CH2:31][CH2:30][NH:8][CH2:9][CH:10]([OH:29])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([CH3:24])[C:22]([C:25]([F:28])([F:26])[F:27])=[N:21][N:20]=2)=[CH:17][CH:18]=1)(=[O:42])[NH2:41]

Participants

4

Reactant 1

HCID 20255099HCID 20255099, compound

Product 1

HCID 20255197HCID 20255197, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

With the addition of 3.0 g of palladium-on-carbon catalyst (10%), a solution of 16 g of crude 1-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[4-(4-methyl-5-trifluoromethyl-4H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol in 160 ml of methanol is catalytically hydrogenated under normal conditions until, after 35 hours, the calculated quantity of hydrogen has been absorbed (an additional quantity of 2 g of catalyst is required for this purpose). Filtration and concentration by evaporation of the filtrate produce a semi-solid mass which, by recrystallisation from isopropanol using active carbon, yields 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(4-methyl-5-trifluoromethyl-4H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol having a melting point of 151°-153°.

Workup

  1. customafter 35 hours
  2. customthe calculated quantity of hydrogen has been absorbed (an additional quantity of 2 g of catalyst
  3. filtrationFiltration and concentration
  4. customby evaporation of the filtrate
  5. customproduce a semi-solid mass which
  6. customby recrystallisation from isopropanol using active carbon

Sources & evidence

ORD record
ord-66ee57a7dd194fc1a6b03e58037287eb
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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