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Triethylamine → Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamate

HRID 1247600
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HRID 1247600 반응식
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Br)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Si:23]([O:30][CH2:31][CH2:32][N:33]([CH2:41][C:42]#[CH:43])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(N(CC)CC)C>[Cu]I.C(#N)C>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:43]#[C:42][CH2:41][N:33]([CH2:32][CH2:31][O:30][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:37])[CH3:38])[CH:15]=3)=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11324466tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamateHCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

생성물 1

HCID 69539588Tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynyl(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamate수율 47.1%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 6342Acetonitrile용매

실험 절차

The sub-titled compound was prepared from N-(1 adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 2(i)) (0.37 g), tert-butyl (2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)prop-2-yn-1-ylcarbamate (Example 11(i)) (0.54 g), copper (I) iodide (0.004 g), bis-triphenyphosphine palladium dichloride (0.014 g), triethylamine (6 ml) and anhydrous acetonitrile (6 ml) by the method of Example 2(iii). The crude product was purified by chromatography on silica gel eluting with, iso-hexane:ethyl acetate (8:1 to 4:1) to afford the sub-titled compound (0.28 g) as a yellow gum.

후처리

  1. customThe crude product was purified by chromatography on silica gel eluting with, iso-hexane:ethyl acetate (8:1 to 4:1)

출처 및 근거

ORD 기록
ord-f4dc023fc5f34f59b6e31647b70a9856
출처 데이터셋
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07129246B2

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