Methylamine → HCID 59170746, compound

HRID 1362707Notes

Reaction equation

HRID 1362707 reaction equation
C1C=CC2N(O)N=[N:7][C:5]=2C=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([N:22]2[CH2:27][CH2:26][CH2:25]/[C:24](=[CH:28]\[C:29]3[CH:34]=[CH:33][C:32]([N:35]4[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]4)=[C:31]([O:41][CH3:42])[CH:30]=3)/[C:23]2=[O:43])[C:19](O)=[O:20])=[CH:14][CH:13]=1.CN.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([N:22]2[CH2:27][CH2:26][CH2:25]/[C:24](=[CH:28]\[C:29]3[CH:34]=[CH:33][C:32]([N:35]4[CH:39]=[C:38]([CH3:40])[N:37]=[CH:36]4)=[C:31]([O:41][CH3:42])[CH:30]=3)/[C:23]2=[O:43])[C:19]([NH:7][CH3:5])=[O:20])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 66961844HCID 66961844, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59170746HCID 59170746, compoundYield 86.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1 N aqueous solution of sodium hydroxide (0.8 mL) was added to a solution of a solution of methyl (E)-(4-fluorophenyl)-(3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-2-oxopiperidin-1-yl)acetate synthesized by the method described in Example 924 (74 mg) in methanol (3 mL), and the reaction solution was stirred at room temperature for 13 hours. 2 N hydrochloric acid (0.4 mL) was added to the reaction solution, and the reaction solution was concentrated under reduced pressure to obtain 72 mg of crude (E)-(4-fluorophenyl)-(3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-2-oxopiperidin-1-yl)acetic acid. HOBT (16 mg) and EDC (23 mg) were added to a solution of the resulting crude (E)-(4-fluorophenyl)-(3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-2-oxopiperidin-1-yl)acetic acid (36 mg) and methylamine (2M THF solution, 0.4 mL) in DMF (3 mL), and the reaction solution was stirred at room temperature for 5 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: ethyl acetate->ethyl acetate:methanol=9:1) to obtain 32 mg of the title compound. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: ethyl acetate->ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-2c5fa3f57f3040669b719fac95a9f116
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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