Pyridine → HCID 72474696, compound

HRID 2252092Notes

Reaction equation

HRID 2252092 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[C:27]([CH3:35])[CH:26]=3)[CH:19]=2)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:37]([O:39][NH2:40])C.N1C=CC=CC=1>C(O)C.CCOC(C)=O>[CH3:37][O:39][N:40]=[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:35])[CH:26]=2)[CH:19]=1)[CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 58958057HCID 58958057, compound

Product 1

HCID 72474696HCID 72474696, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 209 (0.40 g, 0.86 mmol), ethoxyamine hydrochloric acid (0.22 g, 2.63 mmol,) and pyridine (0.19 g, 2.47 mmol) in anhydrous ethanol (3.0 mL) was heated under reflux overnight. The reaction was allowed to cool to room temperature and diluted with EtOAc (100 mL). Upon sequential washings with 1 N NaOH (2×100 mL) and brine (100 mL), the organic solution was dried over Na2SO4 and evaporated to dryness. The resulting residue was purified via flash silica gel chromatography to give the desired product (100 mg, 24%) as a white foam.

Workup

  1. temperatureunder reflux overnight
  2. washUpon sequential washings with 1 N NaOH (2×100 mL) and brine (100 mL)
  3. dry with materialthe organic solution was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe resulting residue was purified via flash silica gel chromatography

Sources & evidence

ORD record
ord-59b5dd4baa7b4e709340ad76ad548f2a
Source dataset
uspto-grants-2008_01
Patent number
US07320989B2

Reaction notes

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