Methanol → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(2-methyl-6-(pyrrolidin-3-yl)pyridin-3-yl)benzenesulfonamide

HRID 594158Notes

Reaction equation

HRID 594158 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]3[C:24]([CH3:41])=[N:25][C:26]([CH:29]4[CH2:33][CH2:32][N:31](CC5C=CC=CC=5)[CH2:30]4)=[CH:27][CH:28]=3)[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:42])[O:4][N:3]=1.ClC(OC(Cl)C)=O.CO>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:23]3[C:24]([CH3:41])=[N:25][C:26]([CH:29]4[CH2:33][CH2:32][NH:31][CH2:30]4)=[CH:27][CH:28]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:42])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 117925766N-(6-(1-benzylpyrrolidin-3-yl)-2-methylpyridin-3-yl)-4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutylbenzenesulfonamide

Product 1

HCID 721944264-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isobutyl-N-(2-methyl-6-(pyrrolidin-3-yl)pyridin-3-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-{[(3,5-dimethyl-4-isoxazolyl)methyl]oxy}-N-{2-methyl-6-[1-(phenylmethyl)-3-pyrrolidinyl]-3-pyridinyl}-N-(2-methylpropyl)benzenesulfonamide (114 mg, 0.194 mmol) in acetonitrile (3 mL) was added 1-chloroethyl chloroformate (0.027 mL, 0.252 mmol) and the reaction mixture was heated at reflux under nitrogen for 2 hours. To this was added methanol (3 mL) and the reaction mixture was refluxed under nitrogen for 1 hour. The solvent was removed in vacuo. The sample was then purified by mass directed autoprep (formic acid buffered) to give the required product as formic acid salt (33 mg). LCMS (2 min, formic) Rt 0.86 min, m/z (ES+) 499 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. temperaturethe reaction mixture was refluxed under nitrogen for 1 hour
  4. customThe solvent was removed in vacuo
  5. customThe sample was then purified by mass

Sources & evidence

ORD record
ord-19e5a9105ac74cc2b7624f8eb97e5c62
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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