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

HRID 985090Notes

Reaction equation

HRID 985090 reaction equation
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]

Participants

3

Reactant 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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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, 3H), 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, 1H).

Workup

  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.

Sources & evidence

ORD record
ord-2f4ce2af81f34f46826abbb2aa976f87
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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