Methanesulfonyl chloride → HCID 86684816, compound

HRID 1527983Notes

Reaction equation

HRID 1527983 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[N:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:36])[CH2:15][C@H:16]([C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:6][O:7][C:8]1[N:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14](=[O:36])[CH2:15][C@H:16]([C:24]1[CH:25]=[CH:26][C:27]([CH:30]2[CH2:31][CH2:32][N:33]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:34][CH2:35]2)=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86684814HCID 86684814, compound

Product 1

HCID 86684816HCID 86684816, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (35 mg, 0.31 mmol) was added at 0° C. to a solution of (R)-1-(3-methoxypyridazin-4-yl)-3-(4-(piperidin-4-yl)phenyl)-3-o-tolylpropan-1-one (64 mg, 154 μmol) and N,N-diisopropylethylamine (79.6 mg, 0.62 mmol) in dichlormethane (2.5 mL). The ice bath was removed, then after 1 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2, heptane/ethyl acetate gradient) produced the title compound (60 mg, 79%). Light yellow gum, MS: 494.3 [M+H]+.

Workup

  1. customThe ice bath was removed
  2. customafter 1 h the reaction mixture was partitioned between sat. aq. ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-19c7fadedc1b439a8fa9770a1291e56c
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

Loading…