Hydroxyamine hydrochloride → 686347-58-0

HRID 1246829Notes

Reaction equation

HRID 1246829 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]2)=[CH:4][CH:3]=1.Cl.[NH2:32][OH:33]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[N:24]2[CH2:29][CH2:28][C:27](=[N:32][OH:33])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21905841686345-96-0

Product 1

HCID 21905790686347-58-0

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-piperidin-4-one 7A-96 (75 mg, 0.17 mmol) and hydroxylamine hydrochloride (11.9 mg, 0.17 mmol) in methanol (0.3 ml) was stirred overnight at room temperature. The reaction was then extracted from saturated aqueous sodium bicarbonate, the combined organic layers were dried (Na2SO4) and concentrated to afford title compound 32A-1 (75 mg, 97%) as a solid: +ESI MS (M+1) 453.4; 1H NMR (400 MHz, DMSO-d6) δ 10.49 (s, 1H), 8.28 (s, 1H), 7.70 (dd, J=7.7, 1.5 Hz, 1H), 7.53–7.41 (m, 5H), 7.31 (d, J=8.7 Hz, 2H), 4.45–4.18 (v br s, 4H), 2.61 (t, J=6.0 Hz, 2H), 2.39 (t, J=5.8 Hz, 2H).

Workup

  1. extractionThe reaction was then extracted from saturated aqueous sodium bicarbonate
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5d685d758b6949e28adf06425086674d
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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