Hydrochloric Acid → 6-(N,N-Dimethylamino-carbonyl)-2,3-dimethyl-8-(trans-1,2,3,4-tetrahydro-2-hydroxy-1-naphthalenyloxy)-imidazo[1,2-a]pyridine hydrochloride

HRID 2053043Notes

Reaction equation

HRID 2053043 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]([OH:16])[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=1)=[O:4].[O:18]1[CH:20]2[CH2:21][CH2:22][C:23]3[C:28]([CH:19]12)=[CH:27][CH:26]=[CH:25][CH:24]=3.C(N(CC)CC)C.[ClH:36]>C(O)C.O.C(OCC)(=O)C.C(OCC)C>[ClH:36].[CH3:17][N:2]([CH3:1])[C:3]([C:5]1[CH:6]=[C:7]([O:16][C@@H:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22][CH2:21][C@H:20]2[OH:18])[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=1)=[O:4]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 921821,2-Epoxy-1,2,3,4-tetrahydronaphthaleneHCID 237308448-Hydroxy-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide

Product 1

HCID 692913216-(N,N-Dimethylamino-carbonyl)-2,3-dimethyl-8-(trans-1,2,3,4-tetrahydro-2-hydroxy-1-naphthalenyloxy)-imidazo[1,2-a]pyridine hydrochlorideYield 34%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g (4.3 mmol) 6-(N,N-dimethylamino-carbonyl)-8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine in 20 ml ethanol and 5 ml water are added 1.25 g (8.6 mmol) 1,2-epoxy-1,2,3,4-tetrahydro-naphthalene and 1.2 ml triethylamine. After 16 h at 80° C., the mixture is cooled down and partitioned between dichloromethane and saturated aqueous ammonium chloride. The organic layer is separated, dried over anhydrous magnesium sulphate and evaporated. Purification of the residue is achieved by column chromatography on silica gel using ethyl acetate:light petroleum ether (1:1), then dichloro-methane:methanol (20:1). The oil thus obtained is dissolved in ethyl acetate and treated with saturated hydrogen chloride in diethyl ether to give a precipitate which is collected and dried to yield 0.6 g (34%) of the title compound as a colourless solid (m.p. 129° C.).

Workup

  1. temperaturethe mixture is cooled down
  2. custompartitioned between dichloromethane and saturated aqueous ammonium chloride
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customPurification of the residue
  7. customThe oil thus obtained
  8. customto give a precipitate which
  9. customis collected
  10. customdried

Sources & evidence

ORD record
ord-9747b48df6a445ceb19c6c23901598f3
Source dataset
uspto-grants-2008_02
Patent number
US07326718B2

Reaction notes

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