Water → HCID 67327786, compound

HRID 1846158Notes

Reaction equation

HRID 1846158 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][O:35][CH3:36])=[N:11][C:12]([N:16]2C(C)=CC=C2C)=[CH:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO.[OH-].[K+].O>C(O)C.O>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([NH2:16])=[N:11][C:10]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][O:35][CH3:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 443297Hydroxyamine hydrochloride2×HCID 67353250HCID 67353250, compound

Product 1

HCID 67327786HCID 67327786, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To stirred solution containing 240 mg (0.49 mmol) of 3-(benzyloxy)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-2-(10-(methoxymethoxy)decyl)-4-methylpyridine in 10 mL of 9:1 ethanol-water were added 338 mg (4.87 mmol) of hydroxylamine hydrochloride followed by 273 mg (4.87 mmol) of potassium hydroxide. The reaction mixture was then stirred at reflux 6 h. then a second portion of 338 mg (4.87 mmol) of hydroxylamine hydrochloride followed by 273 mg (4.87 mmol) of potassium hydroxide was added and the mixture was stirred at reflux 16 h. The reaction mixture was then poured into 50 mL of water and extracted with two 50-mL portions of dichloromethane. The combined organic layer was washed with a 60-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 9:1 dichloromethane-methanol afforded the expected product as a yellowish oil: yield 113 mg (56%); silica gel TLC Rf 0.45 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ 1.24-1.31 (br m, 12H), 1.63-1.53 (m, 4H), 2.16 (s, 3H), 2.62 (dd, 2H, J=8.0, 8.0 Hz), 3.28 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 4.59 (s, 2H), 4.71 (s, 2H), 5.24 (br s, 2H), 6.16 (s, 1H) and 7.31-7.43 (m, 5H); 13C NMR (CDCl3) δ 16.73, 29.19, 29.40, 29.46, 29.46, 29.48, 29.56, 29.72, 29.84, 32.24, 53.41, 67.85, 75.43, 96.34, 108.08, 127.73, 128.00, 128.00, 128.50, 128.50, 137.41, 142.46, 144.91, 153.46 and 154.13; mass spectrum (APCI), m/z 415.2957 (M+H)+ (C25H39N2O3 requires 415.2961).

Workup

  1. stirringThe reaction mixture was then stirred
  2. temperatureat reflux 6 h.
  3. additionwas added
  4. stirringthe mixture was stirred
  5. temperatureat reflux 16 h
  6. extractionextracted with two 50-mL portions of dichloromethane
  7. washThe combined organic layer was washed with a 60-mL portion of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under diminished pressure
  10. customThe residue was purified by chromatography on a silica gel column (10×3 cm)
  11. washElution with 9:1 dichloromethane-methanol

Sources & evidence

ORD record
ord-7edc20a31d704769b39c34ce5a394935
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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