Dimethylamine → (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}-N,N-dimethylbenzamide

HRID 553902Notes

Reaction equation

HRID 553902 reaction equation
[CH:1]([N:4](C(C)C)[CH2:5]C)(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:46]=[CH:47][C:48]=1[N:49]1[CH:53]=[C:52]([CH3:54])[N:51]=[CH:50]1)/[CH:25]=[C:26]1/[C:27](=[O:45])[N:28]2[C@@H:33]([CH2:34][CH2:35]/1)[CH2:32][CH2:31][CH2:30][C@H:29]2[C:36]1[CH:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][CH:37]=1.CNC.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:46]=[CH:47][C:48]=1[N:49]1[CH:53]=[C:52]([CH3:54])[N:51]=[CH:50]1)/[CH:25]=[C:26]1/[C:27](=[O:45])[N:28]2[C@@H:33]([CH2:34][CH2:35]/1)[CH2:32][CH2:31][CH2:30][C@H:29]2[C:36]1[CH:37]=[CH:38][C:39]([C:40]([N:4]([CH3:5])[CH3:1])=[O:42])=[CH:43][CH:44]=1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24780024(E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoic acidHCID 86585896Sodium bicarbonate water

Product 1

HCID 24780026(E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}-N,N-dimethylbenzamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.03 mL), HOBT (10 mg), and EDC (14 mg) were sequentially added to a solution of (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoic acid (22 mg) and dimethylamine (2 M solution in THF, 0.12 mL) in DMF (2 mL), and the reaction solution was stirred at room temperature for two hours. Then, the reaction solution was further stirred at 100° C. for six hours. The reaction solution was left to cool to room temperature. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate:methanol=9:1) to obtain 19 mg of the title compound. The property values of the compound are as follows.

Workup

  1. stirringThen, the reaction solution was further stirred at 100° C. for six hours
  2. waitThe reaction solution was left
  3. temperatureto cool to room temperature
  4. customthe organic layer was separated
  5. dry with materialThe resulting organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-a5e7151552f24f9792ff0dd7bfa5d245
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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