tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamate

HRID 1247591노트

반응식

HRID 1247591 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](I)[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.[CH2:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]#[CH:25]>C(#N)C.C(N(CC)CC)C>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:25]#[C:24][CH2:23][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[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 물질

5

반응물 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 21906675N-(1-adamantylmethyl)-5-chloro-2-iodoisonicotinamide

생성물 1

HCID 21906674tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamate수율 74.4%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

A suspension of N-(1-adamantylmethyl)-5-chloro-2-iodoisonicotinamide (Example2(i)) (0.43 g) and tert-butyl prop-2-ynylcarbamate, (0.31 g) in anhydrous acetonitrile (5 ml) and triethylamine (5 ml) was purged with nitrogen for 5 minutes and the copper (I) iodide (0.004 g) and bis-triphenyphosphine palladium dichloride (0.014 g) were added. The mixture was stirred under nitrogen for 0.75 hours. The mixture was concentrated and the residue was purified by chromatography on silica gel eluting with acetone:dichloromethane (1:19) to afford the sub-titled compound (0.34 g) as a yellow foam.

후처리

  1. customwas purged with nitrogen for 5 minutes
  2. additionthe copper (I) iodide (0.004 g) and bis-triphenyphosphine palladium dichloride (0.014 g) were added
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by chromatography on silica gel eluting with acetone:dichloromethane (1:19)

출처 및 근거

ORD 기록
ord-8bab744f2d184a70b0f0f08a29c1889c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129246B2

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