Methanesulfonyl chloride → HCID 21906462, Verbindung

HRID 988694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988694
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].C(N(C(C)C)C(C)C)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl.C(#N)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:17]=[C:2]([NH:1][S:43]([CH3:42])(=[O:45])=[O:44])[CH:3]=[CH:4][C:5]=2[NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[N:11][CH:12]=1

Komponenten

6

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 696668525-amino-N-(5-chloropyridin-2-yl)-2-[(1-Boc-piperidin-4-yl)methylamino]benzamide

Produkt 1

HCID 21906462HCID 21906462, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 5-amino-N-(5-chloropyridin-2-yl)-2-[(1-Boc-piperidin-4-yl)methylamino]benzamide (0.55 g, 1.2 mmol) in 12 mL of dichloromethane at 0° C. was treated with ethyldiisopropylamine (231 μL, 1.3 mmol) followed by methanesulfonyl chloride (93 μL, 1.2 mmol). The reaction mixture was allowed to reach room temperature overnight, then it was concentrated in vacuo to a crude residue. The residue was directly applied to an SCX column, which was washed with methanol and allowed to stand overnight. Elution with 1:1 dichloromethane-1 N ammonia in methanol provided yellow fractions, which were combined and concentrated in vacuo to a crude residue. Purification by silica gel chromatography, eluting with 9:1 dichloromethane-2 N ammonia in methanol, afforded solid material which was taken up in acetonitrile and sonicated for several minutes. The resulting suspension was filtered, giving rise to the title compound (0.29 g, 56%) as a pale-yellow solid.

Aufarbeitung

  1. concentrationit was concentrated in vacuo to a crude residue
  2. washwas washed with methanol
  3. waitto stand overnight
  4. washElution with 1:1 dichloromethane-1 N ammonia in methanol provided yellow fractions, which
  5. concentrationconcentrated in vacuo to a crude residue
  6. customPurification by silica gel chromatography
  7. washeluting with 9:1 dichloromethane-2 N ammonia in methanol
  8. customafforded solid material which
  9. customsonicated for several minutes
  10. filtrationThe resulting suspension was filtered

Quellen und Nachweise

ORD-Eintrag
ord-90a77ed61e1a423ca5467d4a43b87617
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635657B1

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