Tetrahydrofuran → (S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-one

HRID 1014728노트

반응식

HRID 1014728 반응식
[C:1]1([C@@H:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12](Br)[CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[C:25](Br)[C:24]([N+]([O-])=O)=[CH:23][N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1([C@@H](N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>C(OCC)(=O)C>[C:1]1([C@@H:7]([N:9]2[C:10]3[CH:11]=[C:12]([C:43]4[CH:42]=[CH:41][CH:40]=[C:23]5[C:24]=4[CH:25]=[CH:26][CH:21]=[N:22]5)[N:13]=[CH:14][C:15]=3[NH:16][C:50]2=[O:49])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 758181-Phenethylamine, (-)-HCID 81531DiisopropylethylamineHCID 160998502,4-Dibromo-5-nitropyridineHCID 86626410((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine

생성물 1

HCID 24984682(S)-1-(1-Phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-C]pyridin-2(3H)-one수율 99%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

((1S)-1-phenylethyl)(2-bromo-5-nitro(4-pyridyl))amine. To a solution containing 2,4-dibromo-5-nitropyridine (500 mg, 1.75 mmol) and diisopropylethylamine (314 uL, 1.80 mmol) in tetrahydrofuran (8 mL) at 0° C. was added (S)-(−)-1-phenylethylamine (225 mg, 1.86 mmol). The reaction was allowed to come to room temperature and stirred for 18 h. The reaction was complete via LCMS and the solution was condensed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated to give the desired product (5.6 g, 99%). MS (ESI) m/z 322 [M+1]+.

후처리

  1. customto come to room temperature
  2. customcondensed under reduced pressure
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2788e98dbc28453c81283d0a3e3d6f05
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981893B2

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