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

HRID 341379Notes

Reaction equation

HRID 341379 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-09588cbae2564359b64dae48301bff61
Source dataset
uspto-grants-2014_11
Patent number
US08895755B2

Reaction notes

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