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Potassium Carbonate → 4-(8-amino-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

HRID 62480
ノート
印刷プレビュー

反応式

HRID 62480 の反応式
Br[C:2]1[N:3]=[C:4]([CH:12]2[CH2:17][CH2:16][N:15]3[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]3[CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[C:6]=12.CC1(C)C(C)(C)OB([C:33]2[CH:51]=[CH:50][C:36]([C:37]([NH:39][C:40]3[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[CH:42][N:41]=3)=[O:38])=[CH:35][CH:34]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:11][C:7]1[C:6]2[N:5]([C:4]([CH:12]3[CH2:17][CH2:16][N:15]4[C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][N:20]=[C:14]4[CH2:13]3)=[N:3][C:2]=2[C:33]2[CH:34]=[CH:35][C:36]([C:37]([NH:39][C:40]3[CH:45]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:43]=[CH:42][N:41]=3)=[O:38])=[CH:50][CH:51]=2)[CH:10]=[CH:9][N:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 712227974-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamideHCID 903041061-Bromo-3-(3-(trifluoro methyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-8-amine

生成物 1

HCID 903041264-(8-amino-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide
収率 54.8%

試薬・触媒・溶媒 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
90 °C

実験手順

The mixture of 1-bromo-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-7-yl)imidazo[1,5-a]pyrazin-8-amine (200 mg, 0.497 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (194.54 mg, 0.497 mmol), Pd(dppf)Cl2 (18.3 mg, 0.025 mmol) and K2CO3 (137.26 mg, 0.995 mmol) in dioxane/H2O (5 mL/0.5 mL) was stirred at 90° C. for 2 h under nitrogen atmosphere. Remove the solvent in vacuo. The mixture was treated with ethyl acetate and water, the organic layer was separated, dried over sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by preparative HPLC separation to give 4-(8-amino-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (0.16 g, yield 50%).

後処理

  1. customRemove the solvent in vacuo
  2. additionThe mixture was treated with ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by preparative HPLC separation

出典と根拠

ORDレコード
ord-9b8f6b561d1f47a4ae5c5e7ae44cb8f0
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09446130B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート