2,3-Diaminobenzoic acid → (S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

HRID 85134

Reaktionsgleichung

Reaktionsgleichung von HRID 85134
[F:1][CH:2]([F:20])[C:3]1[CH:10]=[C:9]([O:11][CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)[CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH2:21][C:22]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.O>[F:1][CH:2]([F:20])[C:3]1[CH:10]=[C:9]([O:11][CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)[CH:8]=[CH:7][C:4]=1[C:5]1[NH:31][C:30]2[CH:29]=[CH:28][CH:27]=[C:23]([C:24]([OH:26])=[O:25])[C:22]=2[N:21]=1

Komponenten

6

Edukt 3

HCID 1980692,3-Diaminobenzoic acidHCID 656671Sodium PyrosulfiteHCID 86653795HCID 86653795, Verbindung

Produkt 1

HCID 67202420(S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of (S)-2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzaldehyde (66; 1.83 g, 6.40 mmol) in DMF (150 ml) was added 2,3-diaminobenzoic acid (1; 0.97 g, 6.40 mmol), and Na2S2O5 (1.82 g, 9.60 mmol). The reaction mixture was stirred at 110° C. for 18 h. It was then cooled to room temperature and diluted with water. The resulting solids were collected by filtration and dried to afford (S)-2-(2-(difluoromethyl)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid 67 as dark yellow solid (0.84 g, 51%). MS (ESI) calcd for C21H20F2N5O5: 418.13; found: 419 [M+H].

Aufarbeitung

  1. temperatureIt was then cooled to room temperature
  2. filtrationThe resulting solids were collected by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6429a796ca9840f98860e61305a0406f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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