4-Methylmorpholine → HCID 90039588, Verbindung

HRID 526008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526008
[F:1][C:2]([F:17])([F:16])[CH:3]([C:5]1[CH2:6][C:7](F)([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:9][CH:10]=1)[NH2:4].[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24]2[CH:31]=[C:30]([C:32](O)=[O:33])[NH:29][C:25]2=[N:26][C:27]=1[CH3:28])=[O:21].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.O>[CH3:28][C:27]1[N:26]=[C:25]2[NH:29][C:30]([C:32](=[O:33])[NH:4][CH:3]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=3)[C:2]([F:17])([F:16])[F:1])=[CH:31][C:24]2=[CH:23][C:22]=1[C:20]([O:19][CH3:18])=[O:21]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86713975HCID 86713975, VerbindungHCID 90039786HCID 90039786, Verbindung

Produkt 1

HCID 90039588HCID 90039588, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,2,2-Trifluoro-1-[3-fluoro-3-(trifluoromethyl)phenyl]ethanamine (2.07 g, 8.54 mmol) was dissolved in N,N-dimethylformamide (6 ml), and 5-(methoxycarbonyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (1.60 g, 6.83 mmol), N-[(1H-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate (2.56 g, 6.83 mmol) and 4-methylmorpholine (2.53 ml, 20.50 mmol) were added. The reaction mixture was stirred at room temperature for 16 h and then water was added. The aqueous phase was extracted three times with ethyl acetate and the extract was dried over sodium sulphate, adsorbed on silica gel and chromatographed with ethyl acetate. This gave 1.74 g (55% of theory) of methyl 6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate. HPLC-MS: log P=3.37; mass (m/z): 460.1 (M+H)+; 1H-NMR (D6-DMSO): δ 2.79 (s, 3H), 3.87 (s, 2H), 6.29-6.32 (m, 1H), 7.50 (s, 1H), 7.70-7.74 (m, 1H), 7.82-7.84 (m, 1H), 8.05 (d, 1H), 8.18 (s, 1H), 8.66 (m, 1H), 9.72-9.74 (m, 1H).

Aufarbeitung

  1. extractionThe aqueous phase was extracted three times with ethyl acetate
  2. dry with materialthe extract was dried over sodium sulphate
  3. customchromatographed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4d0df455f9354ec1a2c7a725b3627ca4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345247B2

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