Isopropylamine → HCID 46932422, Verbindung

HRID 1192076

Reaktionsgleichung

Reaktionsgleichung von HRID 1192076
Cl[Sb-](Cl)(Cl)(Cl)(Cl)Cl.ClOC(N(C)C)=[N+](C)C.[Cl:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([Cl:36])[C:23]=1[S:24][C:25]1[S:29][C:28]([C:30]([OH:32])=O)=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34].[CH:37]([NH2:40])([CH3:39])[CH3:38].C(N(CC)CC)C>ClCCl>[Cl:36][C:22]1[CH:21]=[N:20][CH:19]=[C:18]([Cl:17])[C:23]=1[S:24][C:25]1[S:29][C:28]([C:30]([NH:40][CH:37]([CH3:39])[CH3:38])=[O:32])=[CH:27][C:26]=1[N+:33]([O-:35])=[O:34]

Komponenten

6

Edukt 4

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acidHCID 86664723Chloro-1,1,3,3-tetramethyluronium hexachloroantimonate

Produkt 1

HCID 46932422HCID 46932422, VerbindungAusbeute 57,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Chloro-1,1,3,3-tetramethyluronium hexachloroantimonate (47 mg, 0.1 mmol) was added to a suspension of 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (39 mg, 0.11 mmol) in dichloromethane (1 mL) and the mixture was stirred at ambient temperature for 10 min. A solution of isopropylamine (9 mg, 0.12 mmol) and triethylamine (12 mg, 0.12 mmol) in dichloromethane (0.5 mL) was added to the above mixture and was stirred at ambient temperature for over night. After passing through a ISOLUTE™ PE-AX cartridge to remove excess amines, the resulting mixture was concentrated and the residue was purified by reverse-phase HPLC to afford the title product as a white solid (25 mg, 49% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.0 (2H, s), 8.65 (1H, d), 8.50 (1H, s), 4.0 (1H, m), 1.25 (6H, d). MS m/z: 391.70, 393.80 [M+H]+.

Aufarbeitung

  1. stirringwas stirred at ambient temperature for over night
  2. customto remove excess amines
  3. concentrationthe resulting mixture was concentrated
  4. customthe residue was purified by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0c7ac7762bf64e229dcb91c43cb02e4a
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680139B2

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