1,4-Butanesultam → 2-(4-Fluorobenzyl)-10-methoxy-4-[1-(1,1-dioxido-1,2-thiazinan-2-yl)ethyl]-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

HRID 494132

Reaktionsgleichung

Reaktionsgleichung von HRID 494132
[S:1]1(=[O:8])(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:19][C:20]1[CH:47]=[CH:46][C:23]([CH2:24][N:25]2[C:30](=[O:31])[C:29]3[C:32]([O:41][CH3:42])=[C:33]4[C:38](=[O:39])[N:37]([CH3:40])[CH2:36][CH2:35][N:34]4[C:28]=3[C:27]([CH:43](Cl)[CH3:44])=[N:26]2)=[CH:22][CH:21]=1>CN(C=O)C.C1COCC1>[F:19][C:20]1[CH:47]=[CH:46][C:23]([CH2:24][N:25]2[C:30](=[O:31])[C:29]3[C:32]([O:41][CH3:42])=[C:33]4[C:38](=[O:39])[N:37]([CH3:40])[CH2:36][CH2:35][N:34]4[C:28]=3[C:27]([CH:43]([N:2]3[CH2:3][CH2:4][CH2:5][CH2:6][S:1]3(=[O:8])=[O:7])[CH3:44])=[N:26]2)=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 3035081,4-ButanesultamHCID 2733832Lithium HexamethyldisilazideHCID 688663392-(4-Fluorobenzyl)-10-methoxy-4-(1-chloroethyl)-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Produkt 1

HCID 688680582-(4-Fluorobenzyl)-10-methoxy-4-[1-(1,1-dioxido-1,2-thiazinan-2-yl)ethyl]-8-methyl-7,8-dihydropyrazino[1',2':1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cold (0° C.) solution of 1,2-thiazinane 1,1-dioxide (32 mg, 0.24 mmol) in anhydrous DMF (2 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)amide in THF (0.18 mL, 1M) was added. After stirred at room temperature for 20 minutes, solid 2-(4-fluorobenzyl)-10-methoxy-4-(1-chloroethyl)-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (50 mg. 0.12 mmol) was added and the reaction mixture was stirred at room temperature overnight. The product mixture was concentrated under vacuum. The residue was partitioned between dichloromethane and dilute hydrochloric acid. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to afford the title compound. ES MS M+1=518

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. concentrationThe product mixture was concentrated under vacuum
  3. customThe residue was partitioned between dichloromethane and dilute hydrochloric acid
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c8061f3491e94e598a3a7cf4de697896
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538112B2

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