Sulfuric Acid → (7S,8S,9R)-2,3,8-Trimethyl-7-(2-methoxyethoxy)-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 895598Notes

Reaction equation

HRID 895598 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@:10]([CH3:21])([OH:20])[C@H:9]([OH:22])[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].ClCCl.[CH3:38][O:39][CH2:40][CH2:41]O>>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@:10]([CH3:21])([OH:20])[C@@H:9]([O:22][CH2:41][CH2:40][O:39][CH3:38])[C:8]=3[CH:7]=[CH:6][N:5]2[C:23]=1[CH3:24]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 80192-MethoxyethanolHCID 516892Sodium BicarbonateHCID 10308619(7R,8S,9R)-2,3,8-Trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Product 1

HCID 69106244(7S,8S,9R)-2,3,8-Trimethyl-7-(2-methoxyethoxy)-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Conditions

Temperature
60 °C

Procedure

A mixture of 0.5 g of (7R,8S,9R)-2,3,8-trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine and 0.2 ml of conc. sulfuric acid in 10 ml of 2-methoxyethanol is heated at an oil bath temperature of 60° C. for 24 h and then stirred at room temperature for 40 h. The reaction solution is poured into a mixture of 50 ml of saturated aqueous sodium hydrogencarbonate solution and 50 ml of dichloromethane and vigorously stirred. After separating off the organic phase, the aqueous phase is extracted a further three times with 50 ml of dichloromethane each time, the organic phases are combined, the solvent is stripped off in vacuo and the residue obtained is chromatographed on silica gel (eluent: diethyl ether/diethylamine 1/1). 0.3 g of the title compound is obtained as colorless crystals of melting point 1734° C. (diethyl ether).

Workup

  1. stirringvigorously stirred
  2. customAfter separating off the organic phase
  3. extractionthe aqueous phase is extracted a further three times with 50 ml of dichloromethane each time
  4. customthe residue obtained
  5. customis chromatographed on silica gel (eluent: diethyl ether/diethylamine 1/1)

Sources & evidence

ORD record
ord-bc8c47c3a7a44eb89bdfa6cd4e5bf43a
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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