Dimethylamine, hydrochloride → 4-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acid

HRID 1410601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410601
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1.[NH:22]([CH3:24])[CH3:23].Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1

Komponenten

5

Edukt 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 56961213HCID 56961213, Verbindung2×

Produkt 1

HCID 569593354-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acidAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

30 mg of 4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid (Compound 26) was mixed with 1 mmol Me2NH.HCl and 0.5 ml DIEA in 3 ml DMF and heated to 160° C. for 30 minutes. The solvent was evaporated to dryness and water was added. The solid was filtered and washed with water and dried. The crude was triturated with acetone to obtain 10.5 mg of Compound 47. 1H NMR (DMSO-d6 300 MHz TMS): δ 13.2 (b, 1H), 10.28 (s, 1H), 8.22 (m, 2H), 8.11 (d, 1H), 7.99 (d, 1H), 7.50 (s, 1H), 7.39 (d, 1H), 7.26 (s, 1H), 3.24 (s, 6H), MS (ESI): m/z=309.30 [M+1]+.

Aufarbeitung

  1. customThe solvent was evaporated to dryness and water
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude was triturated with acetone

Quellen und Nachweise

ORD-Eintrag
ord-45497f99ba3f41c18ad2b192fa86af1d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921562B2

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