Water → HCID 131728444, compound

HRID 1927462Notes

Reaction equation

HRID 1927462 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:10]=3[S:11](=[O:14])(=[O:13])[CH2:12][C:6]=2[CH:5]=[C:4]([S:23](Cl)(=[O:25])=[O:24])[CH:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.O>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[C:18]([CH3:19])=[CH:17][C:16]([C:20]([OH:22])=[O:21])=[CH:15][C:10]=3[S:11](=[O:14])(=[O:13])[CH2:12][C:6]=2[CH:5]=[C:4]([S:23]([N:31]2[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]2)(=[O:25])=[O:24])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 131728441HCID 131728441, compound

Product 1

HCID 131728444HCID 131728444, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 49j (0.2 g, 0.45 mmol) and 1-methyl-piperazine (0.08 mL, 0.9 mmol) in dry ethyl acetate was stirred overnight at 25° C., treated with water and extracted with ethyl acetate. The organic layer was washed with dil aqueous HCl (10%, 50 mL), water, brine, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound. Yield: 0.180 g, (80%) 1H NMR (DMSO-d6): δ 2.20 (s, 3H, CH3), 2.30 (s, 4H, CH2), 2.80 (s, 3H, CH3), 3.00 (s, 4H, CH2), 5.40 (s, 2H, CH2), 8.00 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.20 (s, 2H, Ar). MS: m/e (ES+) 501 (M+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with dil aqueous HCl (10%, 50 mL), water, brine
  3. concentrationconcentrated
  4. custompurified

Sources & evidence

ORD record
ord-a614224fd2374a558cf8c3c310863c26
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

Loading…