Pyridine → HCID 86590435, compound

HRID 1990921Notes

Reaction equation

HRID 1990921 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:16]([Cl:17])[C:11]=2[CH:10]=[C:9]1[CH:24]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:27]([O:34][NH2:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N1C=CC=CC=1.[NH4+].[Cl-]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]=[C:16]([Cl:17])[C:11]=2[CH:10]=[C:9]1[CH:24]=[N:35][O:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 102312Benzyloxyamine hydrochlorideHCID 20612419HCID 20612419, compound

Product 1

HCID 86590435HCID 86590435, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the aldehyde 20 (50 mg, 0.14 mmol), O-benzylhydroxylamine hydrochloride (26 mg, 0.16 mmol), and pyridine (12 mg, 0.15 mmol) in CH2Cl2 (2 mL) is stirred at ambient temp. for 5 h, then sat. NH4Cl solution is added, and the mixture is extracted with EtOAc (3×5 mL). The combined extracts are washed with brine and dried over MgSO4. Crystallization of the crude solid from hexanes gives 31 mg (0.067 mmol, 48%) of the title compound as colorless solid, single oxime isomer. MS (ES): m/z 463.0/465.0 (90/48) [MH+], 363.1/365.2 (100/32) [MH+-Boc].

Workup

  1. extractionthe mixture is extracted with EtOAc (3×5 mL)
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. customCrystallization of the crude solid from hexanes

Sources & evidence

ORD record
ord-e87ff47b43bf4e548244637f25f509d2
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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