Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide

HRID 1177552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177552
CN([C:4]([O:8][N:9]1N=NC2C=CC=C[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CNOC.[O:39]1[CH2:44][CH2:43][CH2:42][O:41][CH:40]1[C:45]1[CH:50]=[CH:49][C:48]([C:51]2[S:52][C:53]3[CH:59]=[C:58]([C:60]([OH:62])=O)[CH:57]=[CH:56][C:54]=3[N:55]=2)=[C:47]([F:63])[CH:46]=1>CN(C=O)C.O>[O:39]1[CH2:44][CH2:43][CH2:42][O:41][CH:40]1[C:45]1[CH:50]=[CH:49][C:48]([C:51]2[S:52][C:53]3[CH:59]=[C:58]([C:60]([N:9]([O:8][CH3:4])[CH3:10])=[O:62])[CH:57]=[CH:56][C:54]=3[N:55]=2)=[C:47]([F:63])[CH:46]=1

Komponenten

7

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 671115482-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid

Produkt 1

HCID 866387232-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HBTU (0.80 g, 2.11 mmol) was added to a solution of di-isopropylethylamine (0.61 mL, 3.52 mmol), N,O-dimethylhydroxylamine hydrochloride (0.21 g, 2.11 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylic acid (0.51 g, 1.41 mmol) in DMF (7 mL). The reaction mixture was stirred for 30 min, diluted with water, and extracted with EtOAc three times. The combined extracts were dried (MgSO4), concentrated under vacuum, and purified by silica gel chromatography to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-N-methoxy-N-methylbenzo[d]thiazole-6-carboxamide as an oil. MS (ESI) m/z: Calculated: 402.1; Observed: 403.1 (M++1).

Aufarbeitung

  1. extractionextracted with EtOAc three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated under vacuum
  4. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-357d324dff4a4893838a36d48bbbc423
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

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