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Propargyl bromide → 1-[3-({4-Amino-7-[3-(1-piperidinyl)-1-propyn-1-yl]pyrrolo[2,1-f][1,2,4]triazin-5-yl}carbonyl)phenyl]-3-(2,4-dichlorophenyl)urea

HRID 2108357
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HRID 2108357 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7](Br)[C:8]#[CH:9].[NH2:11][C:12]1[C:17]2=[C:18]([C:22]([C:24]3[CH:25]=[C:26]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])=[O:32])[CH:27]=[CH:28][CH:29]=3)=[O:23])[CH:19]=[C:20](Br)[N:16]2[N:15]=[CH:14][N:13]=1>[Cu]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>[NH2:11][C:12]1[C:17]2=[C:18]([C:22]([C:24]3[CH:25]=[C:26]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])=[O:32])[CH:27]=[CH:28][CH:29]=3)=[O:23])[CH:19]=[C:20]([C:7]#[C:8][CH2:9][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:16]2[N:15]=[CH:14][N:13]=1
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참가 물질

6

반응물 3

HCID 7842Propargyl bromideHCID 8082PiperidineHCID 167397901-{3-[(4-Amino-7-bromopyrrolo[2,1-f][1,2,4]triazin-5-yl)carbonyl]phenyl}-3-(2,4-dichlorophenyl)urea

생성물 1

HCID 576294621-[3-({4-Amino-7-[3-(1-piperidinyl)-1-propyn-1-yl]pyrrolo[2,1-f][1,2,4]triazin-5-yl}carbonyl)phenyl]-3-(2,4-dichlorophenyl)urea수율 62%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418476HCID 178418476, 화합물촉매

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온도
80 °C

실험 절차

A solution of piperidine (2 mL) and propargyl bromide (80 wt % in toluene, 0.02 mL, 0.19 mmol) was purged with argon for 10 minutes. The solution was treated with 95G (20 mg, 0.04 mmol), CuI (1 mg, 0.008 mmol) and PdCl2(PPh3)2 (3 mg, 0.004 mmol). The reaction mixture was heated to 80° C. for one hour and then concentrated. The residue was purified by flash chromatography (SiO2, 0% to 10% MeOH/CH2Cl2) to afford the desired compound (13 mg, 62%). HPLC tR=3.17 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 254 nm). [M+H+]=562.27.

후처리

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (SiO2, 0% to 10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-f37761a994be495cbe329a85c46e07cd
출처 데이터셋
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07514435B2

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