4-Methoxybenzenesulfonyl chloride → ACT-462206

HRID 1466466Notes

Reaction equation

HRID 1466466 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=[C:7]([CH3:9])[CH:8]=1.CCN(C(C)C)C(C)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>CC#N.[Cl-].[Na+].O>[CH3:9][C:7]1[CH:6]=[C:5]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[S:35]([C:32]2[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:34][CH:33]=2)(=[O:37])=[O:36])=[O:12])[CH:4]=[C:3]([CH3:2])[CH:8]=1

Participants

6

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67505940HCID 67505940, compound

Product 1

HCID 40924317ACT-462206Yield 95%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(S)—N-(3,5-dimethylphenyl)pyrrolidine-2-carboxamide hydrochloride (18, 3.299 g; 10.7 mmol) is dissolved in MeCN (40 ml) at rt and DIPEA (4.4 g; 34 mmol) is slowly added over 10 minutes followed by the careful addition of commercially available 4-methoxybenzenesulfonyl chloride (19, 2.8 g; 13.6 mmol). The reaction mixture is stirred for 12 h at rt followed by the addition of brine (50 ml) and the extraction of the product with DCM (3×35 ml). The combined organic layers are dried over MgSO4, filtered and concentrated under reduced pressure to give 3.95 g (95%) of (S)—N-(3,5-dimethylphenyl)-1-((4-methoxyphenyl)sulfonyl)-pyrrolidine-2-carboxamide (Example 26) as amorphous solid. LC-MS: tR=0.83 min; [M+H]+=389.3.

Workup

  1. extractionthe extraction of the product with DCM (3×35 ml)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a107e8e37864aa788598f5ccd79ef48
Source dataset
uspto-grants-2015_04
Patent number
US09000029B2

Reaction notes

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