Ethylene carbonate → HCID 22672577, 화합물

HRID 1006677노트

반응식

HRID 1006677 반응식
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[Li+].C1(=O)O[CH2:27][CH2:26][O:25]1>CN(C)C=O.[I-].C[N+](C)(C)C>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]([NH:5][CH2:4][C:3]3[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:2]=3[O:1][CH2:27][CH2:26][OH:25])=[CH:11][CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

참가 물질

6

반응물 3

HCID 7303Ethylene carbonateHCID 62714Lithium hydrideHCID 22672646HCID 22672646, 화합물

생성물 1

HCID 22672577HCID 22672577, 화합물수율 41.2%

시약·촉매·용매 2

HCID 6381Tetramethylammonium iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 8-(2-hydroxy-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine (0.14 g, 0.5 mmol) in N,N-dimethylformamide (3 ml) was added lithium hydride (0.004 g, 0.51 mmol) and the mixture was stirred for 10 min at 100° C. Ethylene carbonate (0.055 g, 0.63 mmol) was added and the mixture was stirred for 10 min at 130° C. Tetramethylammonium iodide (0.054 g, 0.63 mmol) was added and the mixture was stirred for 12 h. at 140-145° C. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride, washed twice with saturated sodium bicarbonate. The organic layer was separated, dried and evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:6) as eluent to give 0.067 g (41%) of the title compound.

후처리

  1. stirringthe mixture was stirred for 10 min at 130° C
  2. stirringthe mixture was stirred for 12 h. at 140-145° C
  3. customThe solvent was evaporated under reduced pressure
  4. washwashed twice with saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-afce90e256ae459aad69a61a8db2b3d3
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790960B2

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