Dimethylcarbamoyl Chloride → HCID 44136797, compound

HRID 554012Notes

Reaction equation

HRID 554012 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][N:11]([CH3:15])[C:12](Cl)=[O:13].[CH3:16][O:17][C:18]1[CH:19]=[C:20](/[CH:30]=[C:31]2\[CH2:32][CH2:33][C@H:34]3[CH2:39][NH:38][CH2:37][C@@H:36]([C:40]4[CH:45]=[C:44]([F:46])[C:43]([F:47])=[C:42]([F:48])[CH:41]=4)[N:35]3[C:49]\2=[O:50])[CH:21]=[CH:22][C:23]=1[N:24]1[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:10][N:11]([CH3:15])[C:12]([N:38]1[CH2:37][C@@H:36]([C:40]2[CH:45]=[C:44]([F:46])[C:43]([F:47])=[C:42]([F:48])[CH:41]=2)[N:35]2[C:49](=[O:50])/[C:31](=[CH:30]/[C:20]3[CH:21]=[CH:22][C:23]([N:24]4[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]4)=[C:18]([O:17][CH3:16])[CH:19]=3)/[CH2:32][CH2:33][C@H:34]2[CH2:39]1)=[O:13]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 57779746HCID 57779746, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 44136797HCID 44136797, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

IPEA (0.02 mL) and dimethylcarbamyl chloride (0.006 mL) were sequentially added to a solution of (4R*,9aS*)-7-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-4-(3,4,5-trifluorophenyl)octahydropyrido[1,2-a]pyrazin-6-one (20 mg) in methylene chloride (3 mL), and the reaction solution was stirred at 0° C. for one hour and at room temperature for five hours. 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 anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate 1:1->ethyl acetate->ethyl acetate:methanol 4:1) to obtain 17 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate 1:1->ethyl acetate->ethyl acetate:methanol 4:1)

Sources & evidence

ORD record
ord-eb18802a94214bd2941bd5239bb1e723
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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