HCID 20255067, compound → HCID 20255070, compound

HRID 638042Notes

Reaction equation

HRID 638042 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]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:21]([CH3:28])[N:20]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1.[H][H]>[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]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:21]([CH3:28])[N:20]=2)=[CH:17][CH:18]=1)(=[O:42])[NH2:41]

Participants

5

Reactant 2

HCID 20255067HCID 20255067, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20255070HCID 20255070, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

After the addition of 2 g of palladium-on-carbon catalyst (5%), a solution of 22 g of crude 1-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[4-(1-methyl-5-trifluoromethyl-1H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol in 320 ml of methanol is hydrogenated under normal conditions until the calculated quantity of hydrogen has been absorbed (3 hours). The product, which has partly crystallised out, is made into a solution by the addition of 1000 ml of dioxan and heating, the catalyst is filtered off and the filtrate is concentrated by evaporation. The crystalline residue that remains is recrystallised from approximately 400 ml of dioxan and yields 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol having a melting point of 206°-208°.

Workup

  1. customhas been absorbed (3 hours)
  2. customThe product, which has partly crystallised out
  3. additionis made into a solution by the addition of 1000 ml of dioxan
  4. temperatureheating
  5. filtrationthe catalyst is filtered off
  6. concentrationthe filtrate is concentrated by evaporation
  7. customThe crystalline residue that remains is recrystallised from approximately 400 ml of dioxan

Sources & evidence

ORD record
ord-bef1786719714132b0a9f4ee1fbd2f6d
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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