Potassium Carbonate → (7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

HRID 2249710Notes

Reaction equation

HRID 2249710 reaction equation
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([OH:19])[C@H:6]([OH:20])[C@H:5]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NCCO>[OH:19][C@@H:7]1[C:8]2[CH:9]=[CH:10][N:11]3[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]=[C:12]3[C:13]=2[NH:4][C@H:5]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:6]1[OH:20]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69288589(7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridine

Product 1

HCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Procedure

The N-acetyl protecting group is detached from the compound (7R,8R,9R)-10-acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine by heating with potassium carbonate in 2-aminoethanol (temp. 70-100° C.). After extractive workup and crystallization, the title compound is obtained as a colourless solid of m.p. 206-209° C.

Workup

  1. customAfter extractive workup and crystallization

Sources & evidence

ORD record
ord-1bc5c881d2644bb6bae96cf60a35671f
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

Loading…