O-Methylhydroxylamine hydrochloride → HCID 86625323, compound

HRID 646273Notes

Reaction equation

HRID 646273 reaction equation
[NH2:1][C:2]1[N:3]([CH3:30])[C:4](=[O:29])[C:5]([C:20]2[CH:21]=[C:22]([CH:27]=O)[N:23]([CH2:25][CH3:26])[CH:24]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]3[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:6]=1.[ClH:31].[O:32]([NH2:34])[CH3:33]>C1COCC1>[ClH:31].[CH3:33][O:32][N:34]=[CH:27][C:22]1[N:23]([CH2:25][CH3:26])[CH:24]=[C:20]([C:5]2([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]4[C:14]([F:19])=[N:15][CH:16]=[CH:17][CH:18]=4)[CH:8]=3)[C:4](=[O:29])[N:3]([CH3:30])[C:2]([NH2:1])=[N:6]2)[CH:21]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 15949563HCID 15949563, compound

Product 1

HCID 86625323HCID 86625323, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of 4-{2-amino-4-[3-(2-fluoropyridin-3-yl)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}-1-ethyl-1H-pyrrole-2-carbaldehyde (0.10 g; 0.25 mmol), in THF (5 mL), was added methoxylamine hydrochloride (0.021 g; 0.25 eq). The mixture was stirred at reflux temperature for 2 hours. The mixture was cooled and the solvent was evaporated. The residue was dissolved in dichloromethane and washed with water. The dichloromethane solution was dried over MgSO4, filtered and evaporated. The resultant residue was crystallized from ethyl acetate and hexane to yield the title compound, 0.069 g (64% yield), mp 190-193° C., MS (ES) m/z 433.1; [M−H]

Workup

  1. temperatureat reflux temperature for 2 hours
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe dichloromethane solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-028ab865fb03407a8cccb1a66f15b402
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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