Methylamine → HCID 68971298, Verbindung

HRID 727261

Reaktionsgleichung

Reaktionsgleichung von HRID 727261
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@H:10]([CH2:24][C:25](O)=[O:26])[N:9]=2)=[CH:4][CH:3]=1.[CH2:28]([N:30](CC)CC)C.C(Cl)(=O)C(C)(C)C.CN>CN(C)C=O.O.O1CCCC1>[CH3:28][NH:30][C:25](=[O:26])[CH2:24][C@@H:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]12

Komponenten

8

Edukt 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 668281072-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid

Produkt 1

HCID 68971298HCID 68971298, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

(S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (7.0 g) and triethylamine (2.73 ml) are added to a mixed solvent of dimethylformamide (70 ml) and tetrahydrofuran (30 ml). The mixture is cooled to -5° C., and pivaloyl chloride (2.38 ml) is dropwise added at said temperature. Ten minutes later, a solution of methylamine (0.69 g) in dimethylformamide (5 ml) is dropwise added at said temperature, and the mixture is stirred at room temperature for 2 hours. Water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled away, and the residue is recrystallized from water/methanol to give 2.29 g of (S)-N-methyl-4-(4-chloro-phenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a]-[1,4]diazepine-6-acetamide 1/4 hydrate, melting point 143°-145° C.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled away
  5. customthe residue is recrystallized from water/methanol

Quellen und Nachweise

ORD-Eintrag
ord-a9af79cf68fe44bd955b58f6d97777a8
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712274

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