Pyridine → 4'-[4-Bromo-5-(hydroxyiminomethyl)-2-propoxyimidazol-1-ylmethyl]-2'-fluoro-biphenyl-2-carboxylic acid t-butyl ester

HRID 475682Notes

Reaction equation

HRID 475682 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=O)=[C:24]([Br:28])[N:23]=[C:22]3[O:29][CH2:30][CH2:31][CH3:32])=[CH:16][C:15]=2[F:33])=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:35][OH:36].N1C=CC=CC=1>O>[C:1]([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]3[C:25]([CH:26]=[N:35][OH:36])=[C:24]([Br:28])[N:23]=[C:22]3[O:29][CH2:30][CH2:31][CH3:32])=[CH:16][C:15]=2[F:33])=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 59283904HCID 59283904, compound

Product 1

HCID 722457744'-[4-Bromo-5-(hydroxyiminomethyl)-2-propoxyimidazol-1-ylmethyl]-2'-fluoro-biphenyl-2-carboxylic acid t-butyl esterYield 91.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Compound A (4.7 g, 9.0 mmol), hydroxylamine hydrochloride (943 mg, 13.6 mmol), pyridine (60 mL, 740 mmol), and water (30 mL, 1.7 mol) were combined and stirred at room temperature overnight. Additional water (30 mL) was added, and the solids were filtered, washed with water, and dried to yield compound B (4.4 g) as a white solid, which was used without further purification.

Workup

  1. filtrationthe solids were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-bbd75c9b0b764b2ca846e45d5386d9a7
Source dataset
uspto-grants-2014_01
Patent number
US08637562B2

Reaction notes

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