Hydrogen Bromide → (7S,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723387
Br.[OH:2][C@@H:3]1[C:12]2[CH:11]=[CH:10][N:9]3[CH:13]=[C:14]([CH3:16])[N:15]=[C:8]3[C:7]=2[NH:6][C@H:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:4]1[OH:23]>>[OH:2][C@H:3]1[C:12]2[CH:11]=[CH:10][N:9]3[CH:13]=[C:14]([CH3:16])[N:15]=[C:8]3[C:7]=2[NH:6][C@H:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:4]1[OH:23]

Komponenten

3

Edukt 2

HCID 260Hydrogen BromideHCID 10125504(7R,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Produkt 1

HCID 69230549(7S,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a of 0° C. cooled and stirred solution of hydrobromic acid is added 1.00 g (3.39 mmol) (7R,8R,9R)-7,8-dihydroxy-2-methyl 9-phenyl-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine. After 0.5 h the reaction is quenched by adding ice and aqueous ammonia solution until the reaction mixture is transferred to pH 9.8. The precipitated solid is separated, washed with water and dried in vacuo at 60° C. to provide the title compound as a armorph solid. 1H-NMR (200 MHz, [D6] DMSO): δ=2.30 (s, 3 H), 3.84 (m, 1H), 4.34 (t, 1H), 4.48 (dd, 1H), 6.72 (d, 1H.), 7.25–7.45 (m, 5H), 7.56 (d, 1H), 7.73 (d, 1 H).

Aufarbeitung

  1. customAfter 0.5 h the reaction is quenched
  2. additionby adding ice and aqueous ammonia solution until the reaction mixture
  3. customThe precipitated solid is separated
  4. washwashed with water
  5. customdried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-bc1ee604409841a7b30e1e21e706847e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141567B2

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