Acetone → HCID 66558594, compound

HRID 1530528Notes

Reaction equation

HRID 1530528 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[N:11]([CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([O:23][CH:24]([CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)[CH3:25])[CH:20]=[CH:19][C:16]=43)[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH3:32][C:33]([CH3:35])=O>CO.[Pd]>[CH:1]([N:4]1[C:8]([C:9]2[N:18]=[C:17]3[C:16]4[CH:19]=[CH:20][C:21]([O:23][CH:24]([CH:26]5[CH2:31][CH2:30][N:29]([CH:33]([CH3:35])[CH3:32])[CH2:28][CH2:27]5)[CH3:25])=[CH:22][C:15]=4[O:14][CH2:13][CH2:12][N:11]3[CH:10]=2)=[N:7][CH:6]=[N:5]1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 180AcetoneHCID 68313054HCID 68313054, compound

Product 1

HCID 66558594HCID 66558594, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-(1-piperidin-4-ylethoxy)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (211 mg, 0.50 mmol), acetone (6 mL) and 10% Pd/C (150 mg) in MeOH (2 mL) was stirred under an atmosphere of H2 at RT for 16 h. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The resulting residue was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18, on a gradient 10-90%, 0.1% HCO2H acetonitrile/water) to afford 143 (161 mg, 69%). LCMS: RT 3.08 [M+H]+ 465.4. 1H NMR (DMSO, 400 MHz): δ 8.29 (1H, d, J=8.96 Hz), 8.23 (1H, s), 7.90 (1H, d, J=0.64 Hz), 7.85 (1H, s), 6.77 (1H, dd, J=8.99, 2.54 Hz), 6.57 (1H, d, J=2.51 Hz), 5.93-5.85 (1H, m), 4.48 (4H, s), 4.38-4.31 (1H, m), 2.97 (2H, d, J=11.01 Hz), 2.87-2.86 (1H, m), 2.30 (2H, t, J=11.50 Hz), 1.84 (1H, d, J=12.83 Hz), 1.67-1.63 (2H, m), 1.47 (6H, d, J=6.60 Hz), 1.44-1.29 (1H, m), 1.21 (3H, d, J=6.10 Hz), 1.03 (6H, d, J=6.56 Hz)

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting residue was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18

Sources & evidence

ORD record
ord-e92e9288a6b94d7487bef6dfffe58e58
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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