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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate → tert-Butyl 1-(4-(4-((2-(1-carbamoylcyclopropyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate

HRID 592492
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HRID 592492 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:12]([NH2:14])=[O:13])[CH2:11][CH2:10]1)#[CH:2].Cl[C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[C:18]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34])=[CH:29][CH:28]=2)[N:17]=1>CN(C=O)C.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.[Cu]I>[C:12]([C:9]1([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[C:2][C:20]2[C:21]([C:22]([F:23])([F:25])[F:24])=[CH:16][N:17]=[C:18]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([CH:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH3:34])=[CH:31][CH:32]=3)[N:19]=2)[CH2:11][CH2:10]1)(=[O:13])[NH2:14]
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참가 물질

6

반응물 2

HCID 76611269Tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamateHCID 867122761-(2-Ethynylphenyl)cyclopropanecarboxamide

생성물 1

HCID 86712349tert-Butyl 1-(4-(4-((2-(1-carbamoylcyclopropyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A solution of 1-(2-ethynylphenyl)cyclopropanecarboxamide K6 (0.15 g, 0.81 mmol) in DMF (3 mL) was added to a reaction vessel containing tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate A80 (0.34 g, 0.81 mmol), PdCl2(PPh3)2 (0.028 g, 0.040 mmol) tri-tert-butylphosphonium tetrafluoroborate (0.023 g, 0.081 mmol) and copper(I)iodide (0.015 g, 0.081 mmol). The mixture was bubbled with nitrogen for 10 minutes before Et3N (1.5 mL) was added. The mixture was heated at 120° C. under microwave irradiation for 15 minutes. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-100% EtOAc in cyclohexane) to give the title compound A81 as a yellow oil (0.26 g, 56%). LCMS-C: rt 5.80 min; m/z 566 [M+H]+.

후처리

  1. customThe mixture was bubbled with nitrogen for 10 minutes before Et3N (1.5 mL)
  2. additionwas added
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by silica gel column chromatography (Combiflash Rf, 0-100% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-d3b06a80062949b694185bfa34075072
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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