HCID 20237871, compound → HCID 20237810, compound

HRID 1903805Notes

Reaction equation

HRID 1903805 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([O:13][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 20237871HCID 20237871, compound

Product 1

HCID 20237810HCID 20237810, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.0 g. 1-(4-Benzyloxyphenoxy) 3-[2-(indazol-4-ylamino)-ethylamino]-propan-2-ol are hydrogenated in the presence of 0.5 g. palladium-charcoal (10%) in 100 ml. methanol. After filtering off the catalyst with suction, the filtrate is evaporated and the residue is triturated with ethanol. It is then dissolved in hot dimethylformamide, treated with active charcoal, mixed with double the amount of water, filtered off with suction and washed with water and then with ethanol. There are obtained 3.0 g. (76% of theory) of the desired product in the form of pale, pinkish crystals; m.p. 216°-218° C.

Workup

  1. filtrationAfter filtering off the catalyst with suction
  2. customthe filtrate is evaporated
  3. customthe residue is triturated with ethanol
  4. dissolutionIt is then dissolved in hot dimethylformamide
  5. additiontreated with active charcoal
  6. additionmixed with double the amount of water
  7. filtrationfiltered off with suction
  8. washwashed with water
  9. customThere are obtained 3.0 g

Sources & evidence

ORD record
ord-f23e78ec159d4968b4756f4982fec2c3
Source dataset
uspto-grants-1984_03
Patent number
US04438128

Reaction notes

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