Hydroxyamine hydrochloride → HCID 178504674, compound

HRID 423491Notes

Reaction equation

HRID 423491 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]#[N:26])[CH2:21][CH2:20]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[NH2:28][OH:29]>C(O)C>[OH:29][NH:28][C:25]([N:22]1[CH2:21][CH2:20][CH:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=3)=[CH:12][CH:13]=2)[CH2:24][CH2:23]1)=[NH:26]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866387364-({[4'-(Methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrile

Product 1

HCID 178504674HCID 178504674, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture 4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarbonitrile (60 mg, 0.16 mmol) and hydroxylamine hydrochloride (11 mg, 0.16 mmol) in ethanol (5 mL) was heated at 80° C. for 2 h, then cooled to ambient temperature overnight. The mixture was concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 to give 60 mg (93%) of N-hydroxy-4-({[4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboximidamide as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.93 (m, 2H), 7.87 (m, 2H), 7.69 (d, 2H, J=8.8 Hz), 7.05 (d, 2H, J=8.8 Hz), 3.91 (d, 2H, J=6.0 Hz), 3.84-3.74 (m, 2H), 3.22 (s, 3H), 3.02-2.96 (m, 2H), 2.05 (bs, 2H), 1.86-1.76 (m, 2H), 1.36-1.22 (m, 2H); LRMS (ESI), m/z 404 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-56ae9bec07ab45a28bb82b05195fbd9b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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