Acetic Acid → HCID 178432326, compound

HRID 220906Notes

Reaction equation

HRID 220906 reaction equation
C([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]([C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:36][CH2:35]4)=[C:26]([CH3:46])[CH:25]=3)=[O:23])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:47])C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[Pd+2].[OH-]>[CH3:43][C:42]([CH3:45])([CH3:44])[CH2:41][CH2:40][N:37]1[CH2:36][CH2:35][N:34]([CH2:33][CH2:32][CH2:31][O:30][C:27]2[CH:28]=[CH:29][C:24]([C:22]([N:14]3[CH2:13][CH2:12][C:11]4[N:10]=[C:9]([CH3:47])[NH:8][C:17]=4[C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]3=4)=[O:23])=[CH:25][C:26]=2[CH3:46])[CH2:39][CH2:38]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57555278HCID 57555278, compound

Product 1

HCID 178432326HCID 178432326, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(1-Benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulen-6-yl)-(4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-propoxy}-3-methyl-phenyl)-methanone from Example E70.3 (98 mg, 0.15 mmol) was dissolved in methanol (5 ml) and acetic acid (1 ml) and hydrogenated over 20 wt. % palladium hydroxide catalyst (98 mg) for 8 h. The mixture was filtered through glass-fibre paper and the filtrate was concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated NaHCO3 then brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white powder identified as the title compound (17 mg, 20%).

Workup

  1. filtrationThe mixture was filtered through glass-fibre paper
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated NaHCO3
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
  8. customto give a white powder

Sources & evidence

ORD record
ord-06287db756304f02a4f3031f8039d3d4
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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