Pyridine → 1-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

HRID 1449752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449752
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.N1C=CC=CC=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.O>[CH3:37][S:38]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:29])([CH3:30])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2)(=[O:40])=[O:39]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 214776001-[5-Aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Produkt 1

HCID 214776751-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[5-aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine (EXAMPLE 41, 300 mg) in dry methylene chloride (6 ml) under nitrogen is added pyridine (119 μl) and methanesulfonyl chloride (57 μl). The mixture is stirred at 20°-25° for 24 hr and then diluted with methylene chloride (20 ml) and water (8 ml). The layers are separated and the organic phase is washed with saline (8 ml), dried over sodium sulfate, and concentrated to give a solid which is then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi), eluting with methanol/chloroform (2.5/97.5). Pooling of the appropriate fractions, concentration to a solid, and recrystallization from chloroform gives the title compound, mp 232°-233° (decomp).

Aufarbeitung

  1. customThe layers are separated
  2. washthe organic phase is washed with saline (8 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a solid which
  6. customis then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi)
  7. washeluting with methanol/chloroform (2.5/97.5)
  8. concentrationPooling of the appropriate fractions, concentration
  9. customto a solid, and recrystallization from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-348e849b344f4e3ab5c75ea0b6c8b5bc
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05599930

Notizen zur Reaktion

Wird geladen…