Diisopropylethylamine → 5-{(3R)-4-[(3-acetylphenyl)sulfonyl]-3-methylpiperazin-1-yl}pyridine-2-carbonitrile

HRID 1868122Notes

Reaction equation

HRID 1868122 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[N:12][CH:13]=2)[CH2:3]1.[C:16]([C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[CH3:17].C(N(C(C)C)CC)(C)C>ClCCl>[C:16]([C:19]1[CH:20]=[C:21]([S:25]([N:7]2[CH2:6][CH2:5][N:4]([C:8]3[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[N:12][CH:13]=3)[CH2:3][C@H:2]2[CH3:1])(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27562603-Acetylbenzenesulfonyl chlorideHCID 442495865-[(3R)-3-methylpiperazin-1-yl]pyridine-2-carbonitrile

Product 1

HCID 442495875-{(3R)-4-[(3-acetylphenyl)sulfonyl]-3-methylpiperazin-1-yl}pyridine-2-carbonitrileYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-[(3R)-3-methylpiperazin-1-yl]pyridine-2-carbonitrile (250 mg, 1.24 mmol) and 3-acetylbenzenesulfonyl chloride (270.3 mg, 1.24 mmol) in anhydrous dichloromethane (4 mL) was added diisopropylethylamine (0.43 mL, 2.48 mmol). The mixture was stirred at room temperature for over night. Reaction was complete as determined by TLC. The reaction mixture was purified via flash column chromatography to yield 5-{(3R)-4-[(3-acetylphenyl)sulfonyl]-3-methylpiperazin-1-yl}pyridine-2-carbonitrile in 80.3% yield (383 mg) as a light yellow solid.

Workup

  1. customReaction
  2. customThe reaction mixture was purified via flash column chromatography

Sources & evidence

ORD record
ord-326ad8aa2b004662b943d832552f8faf
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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