Pyridine → HCID 136349114, compound

HRID 1908702Notes

Reaction equation

HRID 1908702 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]2[C:5]([C:6](=O)[CH2:7][C:8]3([O:14]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=1.Cl.[O:19]([NH2:21])[CH3:20].N1C=CC=CC=1>CO>[CH3:20][O:19][N:21]=[C:6]1[C:5]2[C:15](=[CH:16][C:2]([OH:1])=[CH:3][CH:4]=2)[O:14][C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 12462879HCID 12462879, compound

Product 1

HCID 136349114HCID 136349114, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 16A (479 mg, 2.06 mmol), methoxylamine hydrochloride (275 mg, 3.29 mmol), and pyridine (0.36 mL, 4.45 mmol) were stirred in methanol (5 mL) at room temperature overnight. After this time, the solvent was evaporated in vacuo, and the residue was taken up in ethyl acetate and washed with 1N HCl and brine. The organic solution was dried over Na2SO4 and was evaporated in vacuo. Chromatography on silica gel (4:1 hexane-ethyl acetate, eluant) afforded the title compound as a colorless oil, 524 mg (97%). 1H NMR (300 MHz, DMSO-d6) δ 9.79 (br, 1H), 7.54 (d, J=8.8 Hz, 1H), 6.35 (m, 1H), 6.22 (m, 1H), 3.84 (s, 3H), 2.68 (s, 2H), 1.25-1.79 (m, 10H). MS (DCI+) m/z 262 (M+H).

Workup

  1. customAfter this time, the solvent was evaporated in vacuo
  2. washwashed with 1N HCl and brine
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-8b32d042f1a247f698eda62254d1b498
Source dataset
uspto-grants-2013_12
Patent number
US08598220B2

Reaction notes

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