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Dimethylformamide → 2-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-({5,6-dichloro-1-[2-(methoxymethoxy)ethyl]-1H-benzimidazol-2-yl}methyl)-N-methylacetamide

HRID 1428403
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HRID 1428403 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH2:16][C:17]3[NH:21][C:20]4[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:19]=4[N:18]=3)[CH3:15])=[O:13])[C:6]=2[CH:28]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[CH2:41][CH2:42][O:43][CH2:44][O:45][CH3:46]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]([CH2:16][C:17]3[N:18]([CH2:41][CH2:42][O:43][CH2:44][O:45][CH3:46])[C:19]4[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[CH:22][C:20]=4[N:21]=3)[CH3:15])=[O:13])[C:6]=2[CH:28]=1
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6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 33310511-Bromo-2-(methoxymethoxy)ethaneHCID 1176525702-(5-chloro-2-oxo-1,3-benzoxazol-3 (2H)-yl)-N-[(5,6-dichloro-1H-benzimidazol-2-yl)methyl]-N-methylacetamide

생성물 1

HCID 1176525882-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-({5,6-dichloro-1-[2-(methoxymethoxy)ethyl]-1H-benzimidazol-2-yl}methyl)-N-methylacetamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a mixture of 2-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-[(5,6-dichloro-1H-benzimidazol-2-yl)methyl]-N-methylacetamide (150 mg) and DMF (4.5 mL) were added K2CO3 (94 mg) and 1-bromo-2-(methoxymethoxy)ethane (80 μL), followed by heating and stirring at 70° C. for 5 hours. The reaction mixture was cooled to room temperature and then diluted with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=50/50-0/100) to obtain 2-(5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-({5,6-dichloro-1-[2-(methoxymethoxy)ethyl]-1H-benzimidazol-2-yl}methyl)-N-methylacetamide (110 mg).

후처리

  1. temperatureby heating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washThe organic layer was washed with water and brine in this order
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=50/50-0/100)

출처 및 근거

ORD 기록
ord-554500ec518845d29f0d8a6299990982
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937087B2

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