Triethylamine → 7-Chloro-6-phenyl-2-phenylsulfamoyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide

HRID 857885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857885
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][NH:15][CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.[C:34]1([NH:40][S:41](Cl)(=[O:43])=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(#N)C>[Cl:8][C:9]1[C:10]([C:24]([NH2:26])=[O:25])=[C:11]2[CH2:16][N:15]([S:41](=[O:43])(=[O:42])[NH:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:14][CH2:13][N:12]2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 11564615Phenylsulfamoyl chlorideHCID 68886670HCID 68886670, Verbindung

Produkt 1

HCID 587620107-Chloro-6-phenyl-2-phenylsulfamoyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amideAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 7-chloro-6-phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide trifluoroacetic acid salt (100 mg, Reference Example 1) in dry acetonitrile (5 mL) was treated with dry triethylamine (0.20 mL), then with phenylsulfamoyl chloride (100 mg Reference Example 44). After stirring at room temperature for a further 1 hour the reaction mixture was evaporated and the residue then treated with water and dichloromethane. The organic phase was separated, then dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1 v/v) to give 7-chloro-6-phenyl-2-phenylsulfamoyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid amide (85 mg) as a white solid, m.p. 207–208° C. [Elemental analysis: C, 55.44; H, 4.34; N, 12.78%; Calculated for C20H19ClN4O3S: C, 55.75; H, 4.44; N, 13.00%].

Aufarbeitung

  1. customwas evaporated
  2. additionthe residue then treated with water and dichloromethane
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. additionThe residue was subjected to column chromatography on silica eluting with a mixture of ethyl acetate and dichloromethane (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-39993faa52474034a0e9d033f6d51584
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148215B2

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