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Tricyclohexylphosphine → 3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 80603
ノート
印刷プレビュー

反応式

HRID 80603 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)[CH:10]=1)=[O:7])#[CH:2].Br[C:30]1[CH:31]=[N:32][C:33]([NH:36][CH:37]2[CH2:39][CH2:38]2)=[N:34][CH:35]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.CCN(C(C)C)C(C)C>[Cu]I.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:37]1([NH:36][C:33]2[N:34]=[CH:35][C:30]([C:2]#[C:1][C:3]3[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:6]([NH:8][C:9]3[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([N:19]4[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]4)[CH:10]=3)=[O:7])=[CH:31][N:32]=2)[CH2:39][CH2:38]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

7

反応物 4

HCID 75806TricyclohexylphosphineHCID 81531DiisopropylethylamineHCID 50233275-bromo-N-cyclopropylpyrimidin-2-amineHCID 866911383-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

生成物 1

HCID 510374083-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒

反応条件

温度
60 °C

実験手順

In a pressure tube with one end sealed, add 192 mg step 3 product, 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.5 mmol), 107 mg Step 4 product, 5-bromo-N-cyclopropylpyrimidin-2-amine (0.5 mmol), 19 mg CuI (0.1 mmol), 2.2 mg Pd(OAc)2 (0.01 mmol), 2.8 mg PCy3 (0.01 mmol) 3.0 mL DMF, 193 mg DIPEA (1.5 mmol), after nitrogen replacement, the solution is heated to 60° C. for 12 h. After cooling to room temperature, the solid is filtered off by 2 cm silical gel column and washed by ethyl acetate for three times, and the solution was concentrated by vacuum evaporation for 193 mg desired product (75%).

後処理

  1. customIn a pressure tube with one end sealed
  2. temperatureAfter cooling to room temperature
  3. filtrationthe solid is filtered off by 2 cm silical gel column
  4. washwashed by ethyl acetate for three times
  5. concentrationthe solution was concentrated by vacuum evaporation for 193 mg desired product (75%)

出典と根拠

ORDレコード
ord-ed4dda5d518b4c6c9f771abe2d26fcae
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846671B2

反応ノート

読み込み中…

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