Dichloromethane → (5)-Methyl 4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate

HRID 62468ノート

反応式

HRID 62468 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=S)=[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.[CH:39]1([C:42]([NH:44][NH2:45])=O)[CH2:41][CH2:40]1.C(Cl)Cl>C1COCC1.[Hg](OC(C)=O)OC(C)=O>[CH:39]1([C:42]2[N:28]3[CH2:29][CH2:30][CH2:31][C@@H:26]([C:13]4[N:9]5[CH:10]=[CH:11][N:12]=[C:7]([NH:6][CH2:5][C:4]6[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:3]=6[O:2][CH3:1])[C:8]5=[C:15]([C:16]5[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=5)[N:14]=4)[C:27]3=[N:45][N:44]=2)[CH2:41][CH2:40]1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 81396CyclopropanecarbohydrazideHCID 90303997(S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-thioxopiperidin-3-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate

生成物 1

HCID 118559027(5)-Methyl 4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate収率 46%

試薬・触媒・溶媒 2

HCID 16683746Diacetyloxymercury触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (S)-methyl 4-(8-((2,4-dimethoxybenzyl)amino)-3-(2-thioxopiperidin-3-yl) imidazo[1,5-a]pyrazin-1-yl)benzoate (600 mg, 1.13 mmol) in THF (20 mL) was added cyclopropanecarbohydrazide (339 mg, 3.39 mmol) and Hg(OAc)2 (360 mg, 1.13 mmol). The mixture was stirred at RT for 20 minutes and then heated to 65° C. overnight. The reaction mixture was filtered and the filtrate was evaporated, the residue was purified by column chromatography on silica gel eluted with EA:DCM:THF=1:1:1 to give (S)-methyl 4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (300 mg, yield 46%).

後処理

  1. temperatureheated to 65° C. overnight
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate 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-f2703c28852a4b00a1ac3032714fde6d
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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