Hydroxylamine → 1-(Naphthalene-2-sulfonyl)-piperazine

HRID 1392968Notes

Reaction equation

HRID 1392968 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=CC=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:15][CH2:14]C(C3SC(C(OC)=O)=CN=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:31]O.O1CCOCC1.[OH-].[Na+]>O>[CH:3]1[C:2]2[C:1](=[CH:25][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][C:4]=1[S:7]([N:10]1[CH2:11][CH2:12][NH:31][CH2:14][CH2:15]1)(=[O:8])=[O:9]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 69201624HCID 69201624, compound

Product 1

HCID 7039571-(Naphthalene-2-sulfonyl)-piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-[1-(1,1′-biphenyl-4-ylsulfonyl)piperidin-4-yl]-1,3-thiazole-5-carboxylate 25.3 (9 mg), 50% hydroxylamine in water (0.05 mL), and dioxane (1 mL) were cooled in ice-water. To the reaction was added 1N sodium hydroxide (0.053 mL) followed by removal of the cooling bath. After stirring overnight, the reaction was neutralized with 1 N hydrochloric acid (0.053 mL) and the solvent evaporated. The residue was purified by preparative hplc to give Example 25 as a floculant white solid (3.5 mg). 1H NMR (DMSO) δ: 2.75 (m, 2H), 2.15 (m, 2H), 2.5 (m, 2H), 3.1 (m, 1H), 3.75 (m, 2H), 7.45-7.55 (m, 3H), 7.72-7.96 (m, 6H), 8.08 (s, 1H), 11.3 (s, 1H); m/e=444 (M+H+).

Workup

  1. customfollowed by removal of the cooling bath
  2. customthe solvent evaporated
  3. customThe residue was purified by preparative hplc

Sources & evidence

ORD record
ord-f85d0dd24f7c4f0ba890260b5bd549ca
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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