Nitrogen → N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

HRID 1527885노트

반응식

HRID 1527885 반응식
[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23](I)[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3].N#N.C(N(CC)C(C)C)(C)C.[CH3:45][Si:46]([C:49]#[CH:50])([CH3:48])[CH3:47]>[Cu]I.CCOC(C)=O.O.CN(C=O)C>[CH3:1][P:2]([CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:29])[C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([C:50]#[C:49][Si:46]([CH3:48])([CH3:47])[CH3:45])[CH:22]=3)=[CH:15][C:14]=2[C:30]([F:33])([F:32])[F:31])[CH2:8][CH2:7]1)([CH3:4])=[O:3]

참가 물질

9

반응물 4

HCID 947NitrogenHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 68911921N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide

생성물 1

HCID 68911889N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-4-methyl-3-[(trimethylsilyl)ethynyl]benzamide

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N-[4-({4-[(dimethylphosphoryl)methyl]piperazin-1-yl}methyl)-3-(trifluoromethyl)phenyl]-3-iodo-4-methylbenzamide (5 mmol), Pd[(PPh3)]4 (289 mg, 0.25 mmol), CuI (71 mg, 0.375 mmol) is placed in a schlenk flask. The flask is subjected to 3 cycles of vacuum-refilling with N2. To this mixture is added anhydrous N,N-diisopropylethylamine (1.1 mL, 6 mmol), DMF (5 mL), and trimethylsilylacetylene (0.92 mL, 6.5 mmol). This solution is stirred at rt for 24 h. Water and EtOAc are added to the reaction mixture to facilitate the extraction. The combined organic layers are dried over Na2SO4, filtered, and then concentrated on a rotavap and the crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas).

후처리

  1. extractionthe extraction
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotavap
  5. customthe crude product is purified on a silica gel column (eluent: 5% MeOH in CH2Cl2, MeON is pre-saturated with ammonia gas)

출처 및 근거

ORD 기록
ord-3df43deea04240a399e6c0476dbef169
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090561B2

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