Acetic Acid → HCID 178432327, compound

HRID 220903Notes

Reaction equation

HRID 220903 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]([F: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[F:46])[CH2:39][CH2:38]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57555403HCID 57555403, compound

Product 1

HCID 178432327HCID 178432327, compoundYield 51%

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-fluoro-phenyl)-methanone from Example E69.3 (90 mg, 0.14 mmol) was dissolved in methanol (5 ml) and acetic acid (1 ml) and hydrogenated over 20 wt. % palladium hydroxide catalyst (90 mg) for 8 h. The mixture was filtered through Celite® filter agent and the filtrate 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% dichloro-methane) to give a white powder identified as the title compound (39 mg, 51%).

Workup

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

Sources & evidence

ORD record
ord-2dab164fcd814d05a2953ede43d2e51b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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