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5-(2-Amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide → 5-[2-Amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide

HRID 1403224
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인쇄 미리보기

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HRID 1403224 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5](I)=[CH:4][N:3]=1.[C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:41]([N:43]2[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]2)=[O:42])=[CH:37][CH:36]=1)#[CH:34]>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=3[CH3:28])=[C:10]([C:29]([NH2:31])=[O:30])[CH:9]=2)[C:5]([C:34]#[C:33][C:35]2[CH:36]=[CH:37][C:38]([C:41]([N:43]3[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]3)=[O:42])=[CH:39][CH:40]=2)=[CH:4][N:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 712395925-(2-Amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamideHCID 71239614(4-Ethynylphenyl)(4-methylpiperazin-1-yl)methanone

생성물 1

HCID 867252955-[2-Amino-5-({4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}ethynyl)pyrimidin-4-yl]-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide수율 80%

시약·촉매·용매 3

HCID 83717
Copper iodide
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a degassed solution of 5-(2-amino-5-iodopyrimidin-4-yl)-2-(5-chloro-2-methylphenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxamide (140 mg, 0.24 mmol), (4-ethynylphenyl)(4-methylpiperazin-1-yl)methanone (98 mg, 0.43 mmol) and TEA (0.335 mL, 2.4 mmol) in dry ACN (2.5 mL) were added copper iodide (2.5 mg, 0.012 mmol) and Pd(PPh3)2Cl2 (8.4 mg, 0.012 mmol). The mixture was heated at 80° C. for 2 h, then the solvent was evaporated. The crude was purified by flash chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 95/4/1) to afford the title compound (131 mg, 80%).

후처리

  1. customthe solvent was evaporated
  2. customThe crude was purified by flash chromatography on silica gel (DCM/MeOH/7N NH3 in MeOH 95/4/1)

출처 및 근거

ORD 기록
ord-16b4ce1d65144cc88652f94335a5f10d
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08912200B2

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