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

HRID 62467노트

반응식

HRID 62467 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7e67814f6b4845a4b67797181e357033
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446130B2

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