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Pyrazole → HCID 66835677, 화합물

HRID 2404425
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HRID 2404425 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[NH:26]1[CH:30]=[CH:29][CH:28]=[N:27]1.[C:31](=[O:34])([O-:33])[O-].[Cs+].[Cs+].CN(C)C=[O:40]>[Cu]I>[C:19]([OH:18])(=[O:40])[C:31]([OH:33])=[O:34].[CH3:25][N:22]1[CH2:23][CH2:24][CH:19]([O:18][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)[CH:3]=2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:20][CH2:21]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 66835733HCID 66835733, 화합물

생성물 1

HCID 66835677HCID 66835677, 화합물

시약·촉매·용매 1

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

반응 조건

온도
120 °C

실험 절차

To a solution of 2-[(3-Bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (208 mg) in N,N-dimethylformamide (1 mL) are added pyrazole (68 mg), cesium carbonate (401 mg) and copper(I) iodide (19 mg). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. for 48 h, the mixture is diluted with water and ammonia solution then extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5). The residue is added to a solution of oxalic acid (1 molar equivalent) and the residual precipitate is filtered and dried to afford 2-[(1-methylpiperidin-4-yloxy)(3-pyrazol-1-ylphenyl)methyl]benzothiazole oxalate melting at 89° C.

후처리

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with water and ammonia solution
  5. extractionthen extracted with ethyl acetate
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5)
  9. additionThe residue is added to a solution of oxalic acid (1 molar equivalent)
  10. filtrationthe residual precipitate is filtered
  11. customdried

출처 및 근거

ORD 기록
ord-1e11e38b032545b1b0a5d1436c580d16
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802664B2

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