Water → 4-[4-Bromo-2-butyl-5-(hydroxyiminomethyl)imidazol-1-ylmethyl]-2,3-difluorobenzoic acid methyl ester

HRID 1693596Notes

Reaction equation

HRID 1693596 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]([CH:16]=O)=[C:14]([Br:18])[N:13]=[C:12]2[CH2:19][CH2:20][CH2:21][CH3:22])=[C:6]([F:23])[C:5]=1[F:24].N1C=CC=CC=1.[OH2:32].[NH2:33]O.Cl>>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:15]([CH:16]=[N:33][OH:32])=[C:14]([Br:18])[N:13]=[C:12]2[CH2:19][CH2:20][CH2:21][CH3:22])=[C:6]([F:23])[C:5]=1[F:24]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866243614-(4-Bromo-2-butyl-5-formyl-imidazol-1-ylmethyl)-2,3-difluorobenzoic acid methyl ester

Product 1

HCID 866243624-[4-Bromo-2-butyl-5-(hydroxyiminomethyl)imidazol-1-ylmethyl]-2,3-difluorobenzoic acid methyl esterYield 83.7%

Procedure

Intermediate (8a) (4.1 g, 10 mmol) was dissolved in pyridine (20 mL, 200 mmol), and water (10 mL, 600 mmol). NH2OH.HCl (898 mg, 12.9 mmol) was added and the mixture was stirred at room temperature overnight. The reaction was quenched by the addition of water (20 mL) and the mixture stirred for 20 minutes. The resulting solid was filtered and dried to yield 3.6 g of intermediate (8b) as a light yellow solid. MS m/z: [M+H+] calcd for C17H18BrF2N3O3, 431.24. found 432.2.

Workup

  1. customThe reaction was quenched by the addition of water (20 mL)
  2. stirringthe mixture stirred for 20 minutes
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-2f7e34fc6d5b4aa0bbeedf392c7e492b
Source dataset
uspto-grants-2012_04
Patent number
US08158659B2

Reaction notes

Loading…