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Pentane → 3-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol

HRID 1698581
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HRID 1698581 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23]([O:25]C)=O)=[CH:4][CH:3]=1.CC[CH2:29][CH2:30][CH3:31].[CH:32]([Li])([CH3:34])[CH3:33]>C(OCC)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][C:12]3[C:17]([CH3:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=3[O:20][CH3:21])[N:7]([CH3:22])[C:6]=2[C:5]([C:23]([OH:25])([CH:30]([CH3:29])[CH3:31])[CH:32]([CH3:34])[CH3:33])=[CH:4][CH:3]=1
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HCID 8003PentaneHCID 67273388Methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylateHCID 178506895HCID 178506895, 화합물

생성물 1

HCID 580123753-{4-Chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazol-7-yl}-2,4-dimethylpentan-3-ol수율 68%

시약·촉매·용매 1

HCID 3283
Diethyl Ether
용매

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온도
0 °C

실험 절차

To a solution of methyl 4-chloro-2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-methyl-1H-benzimidazole-7-carboxylate (200 mg, 0.50 mmol) in diethylether (3 mL) was added dropwise a pentane solution of isopropyl lithium (0.7 M solution, 5 mL) at −78° C., and stirred at 0° C. for 1 h. The reaction mixture was quenched with 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative HPLC eluting with a 5-95% acetonitrile/water gradient mixture to give the title compound (153 mg, 68%).

후처리

  1. customThe reaction mixture was quenched with 6N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative HPLC
  7. washeluting with a 5-95% acetonitrile/water gradient mixture

출처 및 근거

ORD 기록
ord-d591dbd0a0cd461ab48b9583e3930beb
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163935B2

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