Triethylamine → 4-(7-bromo-2H-benzopyran-3-sulfonyl)-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone

HRID 2214826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214826
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12]([NH:14][C:15]1([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][C:30]2=[O:35])[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=2)[CH2:17][CH2:16]1)=[O:13])[CH3:10].[Br:36][C:37]1[CH:50]=[CH:49][C:40]2[CH:41]=[C:42]([S:45](Cl)(=[O:47])=[O:46])[CH2:43][O:44][C:39]=2[CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:36][C:37]1[CH:50]=[CH:49][C:40]2[CH:41]=[C:42]([S:45]([N:32]3[CH2:33][CH2:34][N:29]([CH2:28][C:15]4([NH:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:16][CH2:17][N:18]([C:21]5[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=5)[CH2:19][CH2:20]4)[C:30](=[O:35])[CH2:31]3)(=[O:46])=[O:47])[CH2:43][O:44][C:39]=2[CH:38]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 219483121-{[4-Ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone HydrochlorideHCID 219483277-bromo-2H-benzopyran-3-sulfonyl chloride

Produkt 1

HCID 219483044-(7-bromo-2H-benzopyran-3-sulfonyl)-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinoneAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (253 mg) was added to a solution of 1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone hydrochloride (258 mg) in dichloromethane (15 ml), 7-bromo-2H-benzopyran-3-sulfonyl chloride (233 mg) was added at 0° C., and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added an aqueous sodium carbonate solution, the mixture was extracted with dichloromethane, dried, concentrated, and purified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1) to obtain colorless amorphous 4-(7-bromo-2H-benzopyran-3-sulfonyl)-1-{[4-ethoxycarbonylamino-1-(2-methyl-4-pyridyl)-4-piperidinyl]methyl}-2-piperazinone (169 mg).

Aufarbeitung

  1. additionwas added at 0° C.
  2. extractionthe mixture was extracted with dichloromethane
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography (dichloromethane:10% aqueous ammonia-containing methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-54c839dfbad945ed92e1ae90a3af4353
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109200B2

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