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2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amide → 2-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amide

HRID 1819275
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HRID 1819275 반응식
[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[C:14](I)[CH:13]=[C:12]([CH3:17])[C:11]=2[NH:18][C:19]([C:21]2[N:22]([C:30]3[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[N:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=2)=[O:20])=[O:9])([CH:4]2[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[C:37]([Cu])#[N:38]>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([NH:7][C:8]([C:10]2[CH:15]=[C:14]([C:37]#[N:38])[CH:13]=[C:12]([CH3:17])[C:11]=2[NH:18][C:19]([C:21]2[N:22]([C:30]3[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[N:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=2)=[O:20])=[O:9])([CH:4]2[CH2:6][CH2:5]2)[CH2:3][CH2:2]1
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참가 물질

5

반응물 2

HCID 578872022-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amideHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 709604762-(3-Chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1-ylcarbamoyl)-4-cyano-6-methyl-phenyl]-amide수율 101.2%

시약·촉매·용매 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

To a solution of 3.29 g (5.23 mmol) 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid [2-(bicyclopropyl-1 -ylcarbamoyl)-4-iodo-6-methyl-phenyl]-amide in 50 ml tetrahydrofuran is added 1.19 g (6.25 mmol) Cul, 0.30 g tetrakis(triphenylphosphine) palladium and 2.78 g (31.0 mmol) CuCN. The mixture is heated 1 h at 80° C. and turns dark green. After cooling down, the mixture is filtered on Hyflo and evaporated. The residue is dissolved in 15 ml DMF and poured into 100 ml water containing 5 g NaHCO3. After 30 min stirring, the crystals are filtered, washed with water and a mixture of hexane/acetone (1:3) to afford 2.8 g of the title compound.

후처리

  1. temperatureAfter cooling down
  2. filtrationthe mixture is filtered on Hyflo
  3. customevaporated
  4. dissolutionThe residue is dissolved in 15 ml DMF
  5. additionpoured into 100 ml water containing 5 g NaHCO3
  6. filtrationthe crystals are filtered
  7. washwashed with water
  8. additiona mixture of hexane/acetone (1:3)

출처 및 근거

ORD 기록
ord-62df47719f6049d1a931a7d7ec5facfb
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07601743B2

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