HCID 20255111, compound → HCID 20255186, compound

HRID 638055Notes

Reaction equation

HRID 638055 reaction equation
C([N:8]([CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([C:39](=[O:41])[NH2:40])[CH:33]=1)[CH2:9][CH:10]([OH:28])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>[Pd].CO>[C:39]([C:34]1[CH:33]=[C:32]([CH:37]=[CH:36][C:35]=1[OH:38])[O:31][CH2:30][CH2:29][NH:8][CH2:9][CH:10]([OH:28])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[S:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[N:23]=2)=[CH:17][CH:18]=1)(=[O:41])[NH2:40]

Participants

4

Reactant 1

HCID 20255111HCID 20255111, compound

Product 1

HCID 20255186HCID 20255186, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

After the addition of a total of 5 g of palladium-on-carbon catalyst (5%), a solution of 2.95 g of crude 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-thiazol-2-yl]-phenoxy]-2-propanol in 80 ml of methanol is hydrogenated at 60° and a pressure of 4 bar until the absorption of hydrogen has ceased, the reaction product partly precipitating out of the solution. The suspension is diluted with 50 ml of dioxan/methanol, heated and filtered through a filter aid. The filtrate is freed of solvent in a rotary evaporator and the residue is recrystallised twice from methanol, yielding 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-[4-(trifluoromethyl)-thiazol-2-yl]-phenoxy]-2-propanol having a melting point of 202°-203°.

Workup

  1. customis hydrogenated at 60°
  2. customa pressure of 4 bar until the absorption of hydrogen
  3. customthe reaction product partly precipitating out of the solution
  4. additionThe suspension is diluted with 50 ml of dioxan/methanol
  5. temperatureheated
  6. filtrationfiltered through a filter aid
  7. customThe filtrate is freed of solvent in a rotary evaporator
  8. customthe residue is recrystallised twice from methanol

Sources & evidence

ORD record
ord-dd81fa02f45c4be384fdfc78b28f64ac
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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