Hydrochloric Acid → HCID 19854824, compound

HRID 1649793Notes

Reaction equation

HRID 1649793 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:39])[CH2:10][N:11](CC2C=CC=CC=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:20]#[C:21][C:22]2[N:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=2)=[CH:4][C:3]=1[Cl:40].Cl>C(O)C.[Pd]=O>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([OH:39])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[N:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:24][CH:23]=2)=[CH:4][C:3]=1[Cl:40]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19854778HCID 19854778, compound

Product 1

HCID 19854824HCID 19854824, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[6-[3-[[6-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl](phenylmethyl)amino]hexyl]oxy]-1-propynyl]-3-pyridinyl]acetamide (1 g) was hydrogenated over palladium oxide on carbon (50% aqueous paste, 1 g) in ethanol (50 ml) containing hydrochloric acid for 24 h. The catalyst was removed by filtration through hyflo, the solvent was evaporated and the residual oil was partitioned between 8% sodium bicarbonate solution (150 ml) and ethyl acetate (150 ml). The combined organic extracts were dried and concentrated to give an oil. Purification by FCC eluting with System A (95:5:1) gave an oil which was triturated under ether (50 ml) to give the title compound as a white solid (250 mg) m.p. 66°-67°.

Workup

  1. customThe catalyst was removed by filtration through hyflo
  2. customthe solvent was evaporated
  3. customthe residual oil was partitioned between 8% sodium bicarbonate solution (150 ml) and ethyl acetate (150 ml)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customto give an oil
  7. customPurification by FCC
  8. washeluting with System A (95:5:1)
  9. customgave an oil which
  10. customwas triturated under ether (50 ml)

Sources & evidence

ORD record
ord-03caa20c16d441fe883edb1f5d2c31ac
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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