Water → 4-{[(3S)-3-methyl-4-(2-pyridinylcarbonyl)-1-piperazinyl]sulfonyl}benzonitrile

HRID 41316

Reaktionsgleichung

Reaktionsgleichung von HRID 41316
Cl.Cl.[CH3:3][C@H:4]1[CH2:9][NH:8][CH2:7][CH2:6][N:5]1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:11].CCN(C(C)C)C(C)C.[C:27]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)#[N:28].O>C(Cl)Cl>[CH3:3][C@@H:4]1[N:5]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH2:6][CH2:7][N:8]([S:35]([C:32]2[CH:31]=[CH:30][C:29]([C:27]#[N:28])=[CH:34][CH:33]=2)(=[O:37])=[O:36])[CH2:9]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 394974-Cyanobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67222743(2S)-2-methyl-1-(2-pyridinylcarbonyl)piperazine dihydrochloride

Produkt 1

HCID 446119604-{[(3S)-3-methyl-4-(2-pyridinylcarbonyl)-1-piperazinyl]sulfonyl}benzonitrileAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2S)-2-methyl-1-(2-pyridinylcarbonyl)piperazine dihydrochloride (Description 16) (71 mg, 0.255 mmol) in DCM (3 ml) was added DIPEA (0.183 ml, 1.046 mmol) at room temperature and to it was slowly added 4-cyanobenzenesulfonyl chloride (56.6 mg, 0.281 mmol) and the resultant mixture then stirred for 3 h. 5 ml of water and 5 ml of DCM were added and the organic layer separated with a phase separation cartridge and then evaporated under vacuum. The crude material (120 mg) was purified via Biotage (12M silica column) using a gradient [i-hex/EtOAc] ([90/10] to [40/60]). The desired fractions were then collected and concentrated to dryness giving the title compound (48 mg) as a white solid.

Aufarbeitung

  1. customthe organic layer separated with a phase separation cartridge
  2. customevaporated under vacuum
  3. customThe crude material (120 mg) was purified via Biotage (12M silica column)
  4. customThe desired fractions were then collected
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-dc0910905023484a84df89cc4a67cb1f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530478B2

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