Triethylamine → HCID 86712647, 화합물

HRID 1778981노트

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HRID 1778981 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11])#[CH:2].CCN(CC)CC.Cl[C:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][N:25]=[C:24]([NH:32][C:33]2[CH:53]=[CH:52][C:36]([C:37]([N:39]3[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]3)=[O:38])=[CH:35][CH:34]=2)[N:23]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.CCOC(C)=O.[Cu]I>[CH3:13][O:12][C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[C:2][C:26]1[C:27]([C:28]([F:30])([F:29])[F:31])=[CH:22][N:23]=[C:24]([NH:32][C:33]2[CH:34]=[CH:35][C:36]([C:37]([N:39]3[CH2:40][CH2:41][N:42]([C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[CH2:43][CH2:44]3)=[O:38])=[CH:52][CH:53]=2)[N:25]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 45789861Methyl 2-(2-ethynylphenyl)acetateHCID 86712646tert-Butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate

생성물 1

HCID 86712647HCID 86712647, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A solution of methyl 2-(2-ethynylphenyl)acetate (K1) (0.129 g, 0.741 mmol) in DMF (3 mL) and Et3N (344 μL, 2.47 mmol) was added to a mixture of tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate (A22) (0.300 g, 0.617 mmol), PdCl2 (PPh3)2 (0.065 g, 0.093 mmol), CuI (0.018 g, 0.093 mmol) and PPh3 (0.016 g, 0.062 mmol) in DMF (3 mL). The resulting mixture was heated under microwave irradiation at 120° C. for 15 minutes, diluted with EtOAc and passed through a plug of Celite, washing with EtOAc (60 mL). The filtrates were combined and the volatiles were removed in vacuo to give a residue that was purified by silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.) to give the title compound A23 as a yellow oil (0.337 g, 88%); 1H NMR (400 MHz, CDCl3) δ 8.67 (s, 1H), 7.73 (d, J=8.6 Hz, 2H), 7.68 (dd, J=7.7, 1.0 Hz, 1H), 7.61 (s, 1H), 7.48-7.41 (m, 3H), 7.40-7.31 (m, 2H), 3.96 (s, 2H), 3.71 (s, 3H), 3.67-3.37 (m, 8H), 1.47 (s, 9H). LCMS-A: rt 6.393 min; m/z 624.1 [M+H]+.

후처리

  1. washwashing with EtOAc (60 mL)
  2. customthe volatiles were removed in vacuo
  3. customto give a residue that
  4. customwas purified by silica gel column chromatography (Biotage Isolera, 25 g SiO2 cartridge, 0-80% EtOAc in petroleum benzine 40-60° C.)

출처 및 근거

ORD 기록
ord-f525999ec18b466eaaace98db669a59d
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266864B2

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