Hydrochloric Acid → HCID 66961844, compound

HRID 1446562Notes

Reaction equation

HRID 1446562 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:15]2[CH2:20][CH2:19][CH2:18]/[C:17](=[CH:21]\[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:24]([O:34][CH3:35])[CH:23]=3)/[C:16]2=[O:36])[C:11]([O:13]C)=[O:12])=[CH:6][CH:5]=1.Cl>CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([N:15]2[CH2:20][CH2:19][CH2:18]/[C:17](=[CH:21]\[C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:24]([O:34][CH3:35])[CH:23]=3)/[C:16]2=[O:36])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602488HCID 86602488, compound

Product 1

HCID 66961844HCID 66961844, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. customsynthesized by the method
  2. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f4bdd4c43b24457822e7a661b3d51e7
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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