2-Fluoroisonicotinic acid → 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid

HRID 74607

Reaktionsgleichung

Reaktionsgleichung von HRID 74607
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.F[C:22]1[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][N:23]=1>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:22]4[CH:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][N:23]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1

Komponenten

4

Edukt 2

HCID 3453602-Fluoroisonicotinic acidHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Produkt 1

HCID 583864334-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

6.0 g (22 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 1.5 g (11 mmol) 2-fluoropyridine-4-carboxylic acid in 20 mL NMP were stirred overnight at 110° C. The reaction mixture was cooled and the precipitate formed was suction filtered. This was stirred with water, additionally combined with 15% potassium carbonate solution and extracted several times with DCM. The aqueous phase was acidified, the precipitate formed was suction filtered and dried.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe precipitate formed
  3. filtrationfiltered
  4. extractionextracted several times with DCM
  5. customthe precipitate formed
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f467d20d7d5e4573954603921c70bfd7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

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