Dichloromethane → (S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-thioxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate

HRID 62467ノート

反応式

HRID 62467 の反応式
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([C@@H:26]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]3=O)=[N:14][C:15]=2[C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH:10]=[CH:11][N:12]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:48])=CC=1.C(Cl)Cl.C1COCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[N:9]([C:13]([C@@H:26]3[CH2:31][CH2:30][CH2:29][NH:28][C:27]3=[S:48])=[N:14][C:15]=2[C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH:10]=[CH:11][N:12]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 87949Lawesson's reagentHCID 118559029(S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-oxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate

生成物 1

HCID 90303997(S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-thioxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate収率 62%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of (S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-oxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate (940 mg, 1.82 mmol) in toluene (25 mL) was added Lawesson's reagent (1.5 g, 3.65 mmol). The mixture was heated to reflux overnight. The solvent was evaporated and the residue was purified by column chromatography on silica gel eluted with EA:DCM:THF=1:2:1 to give (S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-thioxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate (600 mg, yield 62%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica gel
  5. washeluted with EA

出典と根拠

ORDレコード
ord-7e67814f6b4845a4b67797181e357033
出典データセット
uspto-grants-2016_09
特許番号
US09446130B2

反応ノート

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