Triethylamine → (7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl ester

HRID 1678248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678248
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:15])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.Cl[C:21]([O:23]C)=[S:22].[CH2:25](N(CC)CC)C>C(O)C>[CH3:25][S:23][C:21](=[O:22])[NH:15][C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([C:5]3[S:1][C:2]4[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=4[CH:4]=3)[CH:7]=1)[NH:13][N:12]=[CH:11]2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 554404Methyl chloromethanethioateHCID 59023728HCID 59023728, Verbindung

Produkt 1

HCID 59023854(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl esterAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 530 mg, 2.0 mmol) and methyl chlorothioformate (0.25 mL, 2.8 mmol) in ethanol (10 mL) was added triethylamine (0.56 mL, 4.0 mmol). The reaction mixture was stirred at ambient temperature for about 16 hours and the resulting solid was collected by filtration, washed with water (3×50 mL), and dried to yield (7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl ester (448 mg, 66%); LC/MS (Table 1, Method e) Rt 2.14 min; m/z: [M−H]− 338.

Aufarbeitung

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water (3×50 mL)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e270663c97304f4bb9384348b20cbc6c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008481B2

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