Pyridine → HCID 136349114, compound

HRID 1437500Notes

Reaction equation

HRID 1437500 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-020a5590afe84984989a0af7e83a4eac
Source dataset
uspto-grants-2009_11
Patent number
US07622493B2

Reaction notes

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