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Methyl iodide → (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

HRID 1880074
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HRID 1880074 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][O:28][CH2:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].I[CH3:32]>CN(C=O)C.O>[O:28]1[CH2:27][CH:26]=[C:25]([C:24]2[C:19]([O:18][C:15]3[CH:14]=[CH:13][C:12]([C:10]([C:2]4[N:3]([CH3:32])[C:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[N:1]=4)=[O:11])=[CH:17][CH:16]=3)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:30][CH2:29]1
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참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 59327026(1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone

생성물 1

HCID 59326995(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of (1H-benzo[d]imidazol-2-yl)(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone (0.350 g, 0.881 mmol) in DMF (5 mL) was treated with iodomethane (0.083 mL, 1.321 mmol). The mixture was stirred at RT and after 4 hours, it was diluted with water and extracted (2×) with DCM. The organic portions were combined and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate, reduced and purified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes to afford (4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone as white solid. MS (ESI, pos. ion) m/z: 411.9 (M+1). IC50 (uM) +++++.

후처리

  1. extractionextracted (2×) with DCM
  2. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialThe organic layer was then dried with sodium sulfate
  4. custompurified by column chromatography on silica gel using a gradient of 30 to 80% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-c47fb1978b9244ae9b665e914c4818f6
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318718B2

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