Hydroxyamine hydrochloride → HCID 178526337, compound

HRID 593764Notes

Reaction equation

HRID 593764 reaction equation
[F:1][C:2]1[C:3]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=O)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([OH:14])=[N:10][CH:11]=[N:12][CH:13]=1.Cl.[NH2:25][OH:26]>N1C=CC=CC=1>[F:1][C:2]1[C:3](/[C:15](/[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[N:25]\[OH:26])=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([OH:14])=[N:10][CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178519618(3-Fluoro-4-(4-hydroxypyrimidin-5-yl)pyridin-2-yl)(4-fluorophenyl)methanone

Product 1

HCID 178526337HCID 178526337, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-fluoro-4-(4-hydroxypyrimidin-5-yl)pyridin-2-yl)(4-fluorophenyl)methanone (0.168 g, 0.536 mmol) and hydroxylamine hydrochloride (0.039 g, 0.563 mmol) in Pyridine (Volume: 2.68 ml) was refluxed for 1.5 hr, allowed to cool to room temperature, and then concentrated in vacuo. Solvent was evaporated. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed (required a few drops of MeOH). Purification of the crude material by silica gel chromatography using an ISCO machine (24 g column, 35 mL/min, 1-25% MeOH in CH2Cl2 over 19 min, tr=12 min) gave the title compound (0.123 g, 0.371 mmol, 69.2% yield) as a tan solid. ESI MS (M+H)+=329.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customSolvent was evaporated
  3. dissolutionThe crude material was dissolved in a minimal amount of CH2Cl2
  4. customto be chromatographed (required a few drops of MeOH)
  5. customPurification of the crude material by silica gel chromatography
  6. customan ISCO machine (24 g column, 35 mL/min, 1-25% MeOH in CH2Cl2 over 19 min, tr=12 min)

Sources & evidence

ORD record
ord-d7335161568041c6995b30e8a28bafec
Source dataset
uspto-grants-2016_01
Patent number
US09242967B2

Reaction notes

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