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

HRID 1014728ノート

反応式

HRID 1014728 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

((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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2788e98dbc28453c81283d0a3e3d6f05
出典データセット
uspto-grants-2011_07
特許番号
US07981893B2

反応ノート

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