Hydroxyamine hydrochloride → (NZ)-N-[(4R,6S)-5-(4-chlorophenyl)sulfonyl-4,6-diethyl-4,6-dihydro-1H-pyrazolo[4,5-c]pyridin-7-ylidene]hydroxylamine

HRID 15728Notes

Reaction equation

HRID 15728 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C@@H:16]([CH2:17][CH3:18])[C:15](=O)[C:14]3[NH:20][N:21]=[CH:22][C:13]=3[C@H:12]2[CH2:23][CH3:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC([O-])=O.[Na+].Cl.[NH2:31][OH:32]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C@@H:16]([CH2:17][CH3:18])/[C:15](=[N:31]/[OH:32])/[C:14]3[NH:20][N:21]=[CH:22][C:13]=3[C@H:12]2[CH2:23][CH3:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 46891412(4R,6S)-5-(4-chlorophenylsulfonyl)-4,6-diethyl-5,6-dihydro-1H-pyrazolo[4,3-c]pyridin-7(4H)-one

Product 1

HCID 136146051(NZ)-N-[(4R,6S)-5-(4-chlorophenyl)sulfonyl-4,6-diethyl-4,6-dihydro-1H-pyrazolo[4,5-c]pyridin-7-ylidene]hydroxylamine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of compound 62 (67 mg, 0.17 mmol) in a mixture of MeOH/H2O (5:1, 9 mL) was added NaOAc (141 mg, 1.7 mmol) followed by hydroxylamine hydrochloride (131.6 mg, 1.9 mmol). The resulting solution was stirred at room temperature for a weekend. The solvent was removed by rotary evaporation and the residue was taken up in EtOAc. The organic phase was washed with water, brine and dried (MgSO4). After removal of the solvent under reduced pressure, the crude product was purified by flash chromatography to give a white solid as the product 63 1H NMR (CDCl3) δ 10.28 (bs, 1H), 7.56 (d, J=9.0 Hz, 2H), 7.45 (s, 1H), 7.20 (d, J=9.0 Hz, 2H), 5.48 (dd, J=4.5, 10.5 Hz, 1H), 4.97 (t, J=7.5 Hz, 1H), 2.06-1.96 (m, 1H), 1.91-1.77 (m, 2H), 1.68-1.57 (m, 1H), 1.22 (t, J=6.9 Hz, 3H), 114 (t, J=7.2 Hz, 3H); MS (m/z) 383.0 (M+H)+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customAfter removal of the solvent under reduced pressure
  5. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-3287212bf6014b4088e3bbb0a53915ee
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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