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Cyclopropylacetylene → N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

HRID 1258596
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HRID 1258596 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=2)[C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[N:6]=1.[CH:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.C1(CNCC2CCCCC2)CCCCC1>O1CCCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:25]1([C:28]#[C:29][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=3)[C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[N:6]=2)[CH2:27][CH2:26]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 138823CyclopropylacetyleneHCID 4594378Bis(cyclohexylmethyl)amineHCID 86653147N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

생성물 1

HCID 86653148N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine수율 80%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (150 mg, 0.35 mmol), cyclopropylacetylene (8.44 M in toluene, 84 μL, 0.70 mmol), copper(I) iodide (6.72 mg, 0.03 mmol), tetrakis(triphenylphosphine)palladium(0) (20.4 mg, 0.05 mmol), N,N-dicyclohexylmethylamine (0.30 mL, 1.41 mmol) in degassed tetrahydrofuran (3 mL) was stirred under an Argon atmosphere at room temperature for 24 h. After evaporation of the solvent in vacuo, purification on silica gel afforded N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as a thick oil [116 mg, yield 80%; HPLC/MS: m/z=411 (M+H); logP(HCOOH)=3.99].

후처리

  1. customAfter evaporation of the solvent
  2. customin vacuo, purification on silica gel

출처 및 근거

ORD 기록
ord-f10e53281c1a43f5971cb3bc4da4764d
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466176B2

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