Hydrochloric Acid → 4-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid

HRID 1640242

Reaktionsgleichung

Reaktionsgleichung von HRID 1640242
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10]C)=[O:9])[CH:3]=1.Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:29](=[CH:30][CH:31]=1)[CH2:28][C:18]1([C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]1=[O:27])[CH2:17]2>CC(O)C>[O:27]=[C:19]1[NH:20][C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:26]2[C:18]21[CH2:17][C:16]1[C:29](=[CH:30][CH:31]=[C:14]([NH:13][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=3)[CH:15]=1)[CH2:28]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 12828947Methyl 4-bromopicolinateHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Produkt 1

HCID 581175174-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

0.17 g (0.79 mmol) methyl 4-bromo-pyridine-2-carboxylate and 17 μL (70 μmol) of a 4M aqueous hydrochloric acid solution were added to 0.20 g (0.78 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one in 5.0 mL of 2-propanol. The reaction mixture was refluxed for 2 h, then cooled to RT and evaporated down. The residue was taken up in THF and mixed with 0.50 mL (2.0 mmol) of a 4M aqueous NaOH solution and stirred overnight at RT. The reaction mixture was diluted with water, combined with 0.5 mL conc. HCl and the solvent was eliminated. The precipitated product was suction filtered and dried.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customevaporated down
  3. additionmixed with 0.50 mL (2.0 mmol) of a 4M aqueous NaOH solution
  4. additionThe reaction mixture was diluted with water
  5. filtrationfiltered
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3a962e5ce5be4740a9adb95fe821c143
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110575B2

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