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Pyridine → 7-[4-(4-acetylpiperazin-1-yl)phenyl]-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972771
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HRID 1972771 반응식
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([C:27]4[CH:32]=[CH:31][C:30]([N:33]5[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]5)=[CH:29][CH:28]=4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:45](Cl)(=[O:47])[CH3:46]>ClCCl>[C:45]([N:36]1[CH2:37][CH2:38][N:33]([C:30]2[CH:31]=[CH:32][C:27]([C:19]3[N:20]4[C:25]([C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)=[C:17]([C:12]4[CH:13]=[CH:14][C:15]5[C:10]([CH:11]=4)=[N:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:16]=5)[CH:18]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35]1)(=[O:47])[CH3:46]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 585294985-(2-benzyl-2H-indazol-6-yl)-7-(4-piperazin-1-ylphenyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

생성물 1

HCID 585296057-[4-(4-acetylpiperazin-1-yl)phenyl]-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine수율 26%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

실험 절차

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(4-piperazin-1-ylphenyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.20 mmol) in dichloromethane (2 mL) was added pyridine (23 μL, 0.28 mmol) followed by acetyl chloride (17 μL, 0.24 mmol). The mixture was stirred (rt) overnight. The mixture was diluted with dichloromethane (25 mL) and was washed with H2O (20 mL), brine, and was dried (Na2SO4) and concentrated. The residue was purified by preparative HPLC using a gradient elution from 15% to 50% acetonitrile in water to obtain 28 mg (26%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 8.56 (s, 1 H), 7.97 (d, 2 H), 7.94 (s, 1 H), 7.81 (d, 1 H), 7.66-7.64 (m, 1 H), 7.36-7.26 (m, 5 H), 7.19 (dd, 1 H), 7.06-7.01 (m, 3 H), 5.66 (s, 2. H), 3.62-3.55 (m, 4 H), 3.26-3.21 (m, 2 H), 3.20-3.14 (m, 2 H), 2.05 (s, 3 H); ES-MS m/z 543.33 [M+H]+, HPLC RT (min) 2.65.

후처리

  1. washwas washed with H2O (20 mL), brine
  2. dry with materialwas dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. washa gradient elution from 15% to 50% acetonitrile in water

출처 및 근거

ORD 기록
ord-5b350a7df57e4362ac490187eb8b6a35
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431695B2

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