Water → HCID 58577484, 화합물

HRID 1429988노트

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HRID 1429988 반응식
[CH3:1][N:2]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=2[N:4]=[C:3]1S(C)(=O)=O.[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[C:18]1=[O:33])[CH3:16].[H-].[Na+].O>CC(N(C)C)=O>[CH2:15]([N:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:19]([C:26]2[CH:27]=[CH:28][C:29]([O:32][C:3]3[N:2]([CH3:1])[C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=4[N:4]=3)=[CH:30][CH:31]=2)[C:18]1=[O:33])[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 585777461-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 58577771HCID 58577771, 화합물

생성물 1

HCID 58577484HCID 58577484, 화합물수율 5.8%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

1-Methyl-2-(methylsulfonyl)-4,5,6,7-tetrahydro-1H-benzimidazole (84 mg) was added to a solution of 1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) and NaH (18.8 mg) (60% in mineral oil) in DMA (3 mL) in a microwave vessel. The vessel was sealed and subjected to microwave irradiation (at 120° C. set by IR sensor, fixed hold time: on, Absorption level: High) for 1 h in a Biotage Initiator 60EXP. The mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 20%-100% EtOAc in hexane) to give 1-ethyl-3-{4-[(1-methyl-4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (8.90 mg) as white crystals.

후처리

  1. customThe vessel was sealed
  2. customsubjected to microwave irradiation (at 120° C. set by IR sensor, fixed hold time: on, Absorption level: High) for 1 h in a Biotage Initiator 60EXP
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, eluted with 20%-100% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-5cfca37777f94647b6199ae42554a056
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940758B2

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