Acetic Acid → HCID 66577208, compound

HRID 2379153Notes

Reaction equation

HRID 2379153 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][N:8]1[CH2:29][CH2:28][C:11]2[N:12]([CH:19]([C:22]3C=CC=CC=3)[O:20]C)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[C:9]1=[O:30].[OH-:31].[Na+].[C:33]([OH:36])(=[O:35])[CH3:34]>C(O)C.[Pd]=O>[C:19]([OH:31])(=[O:20])/[CH:22]=[CH:34]\[C:33]([OH:36])=[O:35].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][N:8]1[CH2:29][CH2:28][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[C:9]1=[O:30]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 18957746HCID 18957746, compound

Product 1

HCID 66577208HCID 66577208, compound

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,3,4,5-tetrahydro-2-[(5-methyl-1H-imidazol-4-yl)-methyl]-5-[phenyl(methoxymethyl)]-1H-pyrido[4,3-b]indol-1-one (400 mg) in ethanol (20 ml) and glacial acetic acid (5 ml) was hydrogenated overnight at room temperature and atmospheric pressure over a pre-reduced 10% palladium oxide on carbon catalyst (50% aqueous paste; 100 mg). The reaction mixture was filtered and the residue was washed with ethanol (100 ml). The filtrate was concentrated in vacuo to give an oil, to which was added 2N sodium hydroxide (50 ml). The resulting suspension was extracted with dichloromethane (2×50 ml) and the combined, dried organic extracts were evaporated to give a solid. This was purified by FCC eluting with System A (75:8:1) to give the free base of the title compound as a solid (240 mg) which was then dissolved in dry methanol (50 ml). Maleate formation gave the title compound (261 mg), t.l.c. (System A, 75:8:1) Rf 0.2

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with ethanol (100 ml)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give an oil
  5. extractionThe resulting suspension was extracted with dichloromethane (2×50 ml)
  6. customdried organic extracts were evaporated
  7. customto give a solid
  8. customThis was purified by FCC
  9. washeluting with System A (75:8:1)

Sources & evidence

ORD record
ord-edf1493fbc7f4023b0a5c278e0d04aa0
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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