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Tetrahydrofuran → 12-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaene

HRID 1614977
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인쇄 미리보기

반응식

HRID 1614977 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:28])[CH:5]=[C:6]([CH2:8][NH:9][C:10]2[C:15]([Cl:16])=[CH:14][N:13]=[C:12]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26]Br)[CH:19]=3)[N:11]=2)[CH:7]=1.O1CCCC1.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]2[CH:5]=[C:6]([CH2:8][NH:9][C:10]3[N:11]=[C:12]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH:19]=4)[CH2:24][CH2:25][CH2:26][O:28]2)[N:13]=[CH:14][C:15]=3[Cl:16])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 584679133-Bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol

생성물 1

HCID 4686474912-Bromo-6-chloro-15-oxa-2,4,8,25-tetraazatetracyclo[17.3.1.1(3,7).1(10,14)]pentacosa-1(23),3(25),4,6,10(24),11,13,19,21-nonaene수율 53%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

Into a reaction flask were added 3-bromo-5-{[(2-{[3-(3-bromopropyl)phenyl]amino}-5-chloropyrimidin-4-yl)amino]methyl}phenol (2.97 g, 5.64 mmol), tetrahydrofuran (30 mL), and a solution of sodium hydroxide in water (33.8 mL, 1.0 M). The reaction mixture was stirred at rt over two days. The mixture was filtered, and then the cake was washed with water, MeOH, and EtOAc successively to provide the desired product (1.33 g, 53%) as an off-white powder. LCMS for C20H18BrClN4O (M+H)+: m/z=444.9, 446.9. 1H NMR (400 MHz, DMSO-d6): δ 9.04 (s, 1H), 7.95 (s, 1H), 7.93 (s, 1H), 7.36 (s, 1H), 7.10 (m, 1H), 7.07 (m, 1H), 6.92 (d, J=7.9 Hz, 1H), 6.86 (s, 1H), 6.78 (d, J=7.5 Hz, 1H), 4.42 (d, J=5.5 Hz, 2H), 4.18 (t, 2H), 3.60 (m, 1H), 2.65 (m, 2H), 1.65 (m, 2H).

후처리

  1. filtrationThe mixture was filtered
  2. washthe cake was washed with water, MeOH, and EtOAc successively

출처 및 근거

ORD 기록
ord-b5ace2a8188f431bae375ea1d35edf74
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765727B2

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