Hydrochloric Acid → HCID 178433082, compound

HRID 1887333Notes

Reaction equation

HRID 1887333 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[NH:16][C:17]([C:21]([O:23]CC)=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[NH:16][C:17]([C:21]([OH:23])=[O:22])=[C:18]([CH3:20])[N:19]=2)[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470397HCID 178470397, compound

Product 1

HCID 178433082HCID 178433082, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of ethyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-1H-imidazole-5-carboxylate (0.10 g, 0.28 mmol) in 1 N aqueous sodium hydroxide (2 mL) was stirred at 45° C. for 16 h, and then at 65° C. for 5 h. The reaction mixture was cooled to 0° C. then acidified with 10% aqueous hydrochloric acid to pH ˜2. The precipitate was filtered, washed with water, and then with acetone into a separate flask. The acetone filtrate was concentrated in vacuo and co-concentrated with methanol to dryness (×2). The residue was combined with the solid to afford the title compound (0.060 g, 65%): MS (ES−) m/z 324.2 (M−1).

Workup

  1. waitat 65° C. for 5 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. concentrationThe acetone filtrate was concentrated in vacuo and co-concentrated with methanol to dryness (×2)

Sources & evidence

ORD record
ord-53f3182ac8e14393ae0a8d82e66e6583
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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