Acetic Acid → 4-[1-Hydroxy-2,3-dihydro-1H-inden-4-yl)amino-6,7-dimethoxy-3-quinolinecarboxamide

HRID 1822854

Reaktionsgleichung

Reaktionsgleichung von HRID 1822854
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([C:15]([NH2:17])=[O:16])=[C:6]2[NH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][CH2:22][C:23]2=[O:28].[BH4-].[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>CO.O1CCCC1.O>[OH:28][CH:23]1[C:24]2[C:20](=[C:19]([NH:18][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][C:7]=3[C:15]([NH2:17])=[O:16])[CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:22]1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 221702646,7-Dimethoxy-4-[(1-oxo-2,3-dihydro-1H-inden-4-yl)amino]-3-quinolinecarboxamide

Produkt 1

HCID 221702254-[1-Hydroxy-2,3-dihydro-1H-inden-4-yl)amino-6,7-dimethoxy-3-quinolinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6,7-Dimethoxy-4-[(1-oxo-2,3-dihydro-1H-inden-4-yl)amino]-3-quinolinecarboxamide (0.062 g, 16.4 mmol) was dissolved in a mixture of methanol (7 ml), tetrahydrofuran (4 ml) and water (3 ml). Sodium borohydride was added in portions (3×5 mg) and during 5 min. After 20 min the reaction mixture was acidified with acetic acid and then made alkaline with saturated aqueous sodium hydrogencarbonate and evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed twice with water and evaporated. The residue was dissolved in methanol and water was added. The title compound, which slowly precipitated, was filtered off and dried to give 40 mg (64%). 1H NMR (DMSO-d6): δ 10.68 (1H, s); 8.82 (1H, s); 8.20 (1H, bs); 7.55 (1H, bs); 7.22 (1H, s); 7.07 (1H, t, J 7.5 Hz); 7.04 (1H, t, J 7.4 Hz); 6.75 (1H, s); 6.63 (1H, d, J 7.5 Hz); 5.20 (1H, d, J 5.7 Hz); 5.01 (1H, q, J 6.2 Hz); 3.85 (3H, s); 3.26 (s, moisture signal overlapping); 2.72–2.63 (1H, m); 2.50–2.36 (m, solvent signal overlapping); 2.30–2.20 (1H, m) and 1.76–1.65 (1H, m).

Aufarbeitung

  1. customevaporated
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe organic phase was washed twice with water
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol
  6. additionwater was added
  7. customThe title compound, which slowly precipitated
  8. filtrationwas filtered off
  9. customdried
  10. customto give 40 mg (64%)

Quellen und Nachweise

ORD-Eintrag
ord-c1b931018edb4ea1b0f070455129bae0
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07037925B2

Verknüpfte Notizen

Wird geladen…