Hydroxylamine → 2-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N-hydroxy-N'-methylpropanediamide

HRID 1519665Notes

Reaction equation

HRID 1519665 reaction equation
[NH2:1][OH:2].C1COCC1.C[O:9][C:10](=O)[CH:11]([N:16]([CH3:31])[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:18])[C:12]([NH:14][CH3:15])=[O:13]>C(O)C>[C:22]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:21]=[CH:20][C:19]([C:17]([N:16]([CH3:31])[CH:11]([C:12]([NH:14][CH3:15])=[O:13])[C:10]([NH:1][OH:2])=[O:9])=[O:18])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 712682154-{[1-Methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl

Product 1

HCID 866792532-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N-hydroxy-N'-methylpropanediamideYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50% aqueous solution (0.20 mL) of hydroxylamine was added to a THF (0.25 mL)-ethanol (0.20 mL) solution of 4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl (30 mg) as obtained in Example 1-(1), and the mixture was stirred for 4 hours at room temperature. The solvents were distilled off under reduced pressure, and the resulting residue was purified by preparative silica gel thin-layer chromatography (chloroform/methanol=8/1). Upon addition of IPE, the precipitated solid was separated by filtration, and dried to obtain 2-[(biphenyl-4-ylcarbonyl)(methyl)amino]-N-hydroxy-N′-methylpropanediamide (Compound 1, light yellow solid) (17 mg, 59%).

Workup

  1. distillationThe solvents were distilled off under reduced pressure
  2. customthe resulting residue was purified by preparative silica gel thin-layer chromatography (chloroform/methanol=8/1)
  3. additionUpon addition of IPE
  4. customthe precipitated solid was separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-27a5a982e8d843249e00698e42658e0c
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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