Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86658353, Verbindung

HRID 2192454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192454
CCN(C(C)C)C(C)C.CN([C:13]([O:17][N:18]1N=NC2C=CC=C[C:19]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:34][C:35]1[CH:46]=[CH:45][C:38]2[C:39]([C:42](O)=[O:43])=[N:40][S:41][C:37]=2[CH:36]=1.Cl.CNOC>CN(C=O)C>[Br:34][C:35]1[CH:46]=[CH:45][C:38]2[C:39]([C:42]([N:18]([O:17][CH3:13])[CH3:19])=[O:43])=[N:40][S:41][C:37]=2[CH:36]=1

Komponenten

6

Edukt 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534011926-Bromobenzo(d)isothiazole-3-carboxylic acid

Produkt 1

HCID 86658353HCID 86658353, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIEA (11.7 mL, 67.4 mmol) and HBTU (7.03 g, 18.5 mmol) were added to a solution of 6-bromobenzo[d]isothiazole-3-carboxylic acid (4.35 g, 16.9 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.14 g, 21.9 mmol) in DMF (100 mL). The reaction was stirred at room temperature for 2 hours. The mixture was partitioned between water and EtOAc. The organic layer was washed with aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (hexane:EtOAc, 3:1) to give 6-bromo-N-methoxy-N-methylbenzo[d]isothiazole-3-carboxamide (4.60 g, 91%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 8.12 (m, 2H), 8.59 (d, J=8.8 Hz, 1H), 3.83 (s, 3H), 3.49 (s, 3H).

Aufarbeitung

  1. customThe mixture was partitioned between water and EtOAc
  2. washThe organic layer was washed with aqueous NaHCO3 solution and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane:EtOAc, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-2d362594b2194385bc52e5c07a0afc45
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329709B2

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