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1,2-Dimethoxyethane → 1-(2-Cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-4-[(2-cyclopropyl-4-thiazolyl)methoxy]-2(1h)-pyridinone

HRID 2203113
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HRID 2203113 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]4[N:22]=[C:21]([CH:23]5[CH2:25][CH2:24]5)[N:20]([CH3:26])[C:19]=4[CH:27]=3)[C:11](=[O:28])[CH:10]=2)[N:6]=1.[CH:29]1(B(O)O)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:23]1([C:21]2[N:20]([CH3:26])[C:19]3[CH:27]=[C:15]([N:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:5]5[N:6]=[C:2]([CH:29]6[CH2:31][CH2:30]6)[S:3][CH:4]=5)=[CH:10][C:11]4=[O:28])[CH:16]=[CH:17][C:18]=3[N:22]=2)[CH2:25][CH2:24]1
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참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 1213862714-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

생성물 1

HCID 897026711-(2-Cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-4-[(2-cyclopropyl-4-thiazolyl)methoxy]-2(1h)-pyridinone수율 24.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

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온도
150 °C

실험 절차

A mixture of 4-((2-bromo-1,3-thiazol-4-yl)methoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (54 mg), cyclopropylboronic acid (30.4 mg), tetrakis(triphenylphosphine)palladium (6.8 mg), potassium carbonate (65.3 mg), DME (1.5 ml) and water (0.5 ml) was heated at 150° C. for 20 min under microwave irradiation. The reaction mixture was then cooled to room temperature, poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from EtOH-water to give the title compound (12.2 mg) as a white solid.

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (hexane/EtOAc
  7. customThe resulting solid was recrystallized from EtOH-water

출처 및 근거

ORD 기록
ord-5f03c5b2eb8f4846b2337238d99457e3
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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