Hydroxyamine hydrochloride → 4-{3-[2-Amino-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075676Notes

Reaction equation

HRID 2075676 reaction equation
C(=[N:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:22]2[C:17](=[CH:18][C:19]([S:32][C:33]3[CH:34]=[C:35]([C:39]4([C:45]#[N:46])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH:36]=[CH:37][CH:38]=3)=[CH:20][CH:21]=2)[N:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.NO.C([O-])(=O)C.[K+]>CO>[NH2:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:22]2[C:17](=[CH:18][C:19]([S:32][C:33]3[CH:34]=[C:35]([C:39]4([C:45]#[N:46])[CH2:40][CH2:41][O:42][CH2:43][CH2:44]4)[CH:36]=[CH:37][CH:38]=3)=[CH:20][CH:21]=2)[N:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 866138284-{3-[2-(Benzhydrylidene-amino)-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 670907114-{3-[2-Amino-4-(4-fluoro-phenyl)-quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3d (300 mg, 0.48 mmol), hydroxylamine hydrochloride (67 mg, 0.97 mmol), and potassium acetate (92 mg, 0.97 mmol) was dissolved in MeOH (10 mL) and stirred overnight at room temperature. The reaction was concentrated and purified by silica gel chromatography (30% EtOAc in hexanes) to obtain the desired product, 3e.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4854c5b9dc39445192c0f643efdcd576
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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