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 2053043ノート

反応式

HRID 2053043 の反応式
[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]

参加物

9

反応物 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

生成物 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 hydrochloride収率 34%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-9747b48df6a445ceb19c6c23901598f3
出典データセット
uspto-grants-2008_02
特許番号
US07326718B2

反応ノート

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