Diisopropylethylamine → (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85175

Reaktionsgleichung

Reaktionsgleichung von HRID 85175
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18](O)=[O:19])[C:11]=2[N:10]=1.[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:26][O:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[CH3:23][C:24]1([CH3:38])[O:28][C@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([NH:34][C:18]([C:17]3[C:11]4[N:10]=[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[C:2]([F:1])([F:21])[F:22])[NH:13][C:12]=4[CH:14]=[CH:15][CH:16]=3)=[O:19])[CH:35]=[CH:36][CH:37]=2)[CH2:26][O:25]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58552948HCID 58552948, VerbindungHCID 672016022-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

Produkt 1

HCID 67203479(R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

2-(2-(Trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in NMP (2 mL) along with (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (133; 64.3 mg, 0.288 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added and the resulting reaction mixture was stirred at room temperature for 12 h. The temperature was then raised to 60° C. and the reaction mixture was allowed to stir for an additional 1 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product 134, as a yellow solid (51.5 mg, 42%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperatureThe temperature was then raised to 60° C.
  3. stirringto stir for an additional 1 h
  4. filtrationfiltered
  5. customThe collected solids were further purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-930a91f7a1494d79b2bed38bf4945ef7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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