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Triethylamine → 1-(4-{4-[(2-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 549970
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HRID 549970 반응식
C(N(CC)CC)C.[C:8]([C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1)#[CH:9].I[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]>CN(C)C=O.O.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.[Cu]I>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:9]#[C:8][C:10]1[N:11]=[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:33])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([C:29]([F:30])([F:32])[F:31])=[N:24]3)[CH2:17][CH2:16]2)[S:13][CH:14]=1
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참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 68257o-IodoanisoleHCID 866420471-[4-(4-Ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

생성물 1

HCID 671563421-(4-{4-[(2-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

시약·촉매·용매 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (25 mg), copper(I) iodide (7 mg) and triethylamine (48 mg) are added to a solution of 1-[4-(4-ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (I-86, 150 mg) and 1-iodo-2-methoxybenzene (101 mg) in degassed N,N-dimethylformamide (1.5 ml). After 2 hours of stirring at 85° C., the reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 1-(4-{4-[(2-methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (100 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customAfter chromatographic purification

출처 및 근거

ORD 기록
ord-0fee0cd8f6514434bf9cf9a56dd52971
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943774B2

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