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Triethylamine → 8-[(1S,2S)-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053042
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HRID 2053042 반응식
[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[C@H:20]2[CH2:21][C:22]3[C:27]([C@@H:19]12)=[CH:26][CH:25]=[CH:24][CH:23]=3.C(N(CC)CC)C>C(O)C.O>[OH:18][C@H:20]1[CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:19]1[O:16][C:7]1[C:8]2[N:9]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:10]=[C:5]([C:3]([N:2]([CH3:1])[CH3:17])=[O:4])[CH:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 1512568(1R,2S)-epoxyindaneHCID 237308448-Hydroxy-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide

생성물 1

HCID 104065358-[(1S,2S)-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-(N,N-dimethylamino-carbonyl)-2,3-dimethyl-imidazo[1,2-a]pyridine수율 74%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 962Water용매

실험 절차

To a solution of 1.5 g (6.4 mmol) 6-(N,N-dimethylamino-carbonyl)-8-hydroxy-2,3-dimethyl-imidazo[1,2-a]pyridine in 30 ml ethanol and 7.5 ml water are added 1.7 g (12.9 mmol) (1R,2S)-epoxyindane and 1.8 ml triethylamine. After 3 h at 70° C., the mixture is cooled down and partitioned between dichloro-methane and water. The organic layer is separated, dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using ethyl acetate:light petroleum ether (1:1) and crystallization from diisopropyl ether yields 1.7 g (74%) of the title compound as a colourless solid (m.p. 122° C.).

후처리

  1. temperaturethe mixture is cooled down
  2. custompartitioned between dichloro-methane and water
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customPurification of the residue by column chromatography on silica gel
  7. customethyl acetate:light petroleum ether (1:1) and crystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-ec1612091324462c8531edd9198f1432
출처 데이터셋
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07326718B2

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