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Hydrochloric Acid → N4-{4-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-6-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 2192187
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반응식

HRID 2192187 반응식
[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[F:20])[NH:5][CH:4]=1)[CH3:2].N1C=CC=NC=1N.Cl.Cl[C:30]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]=[C:32]([NH2:40])[N:31]=1.[OH-].[Na+]>O>[CH2:1]([C:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:19]=[CH:18][C:16]([NH:17][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:37])[F:38])[N:33]=[C:32]([NH2:40])[N:31]=3)=[CH:15][C:14]=2[F:20])[NH:5][CH:4]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 313Hydrochloric Acid2회HCID 79782-AminopyrimidineHCID 14798Sodium HydroxideHCID 130869074-Chloro-6-(trifluoromethyl)pyrimidin-2-amineHCID 597410004-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline

생성물 1

HCID 11502907
N4-{4-[(3-Ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluorophenyl}-6-(trifluoromethyl)pyrimidine-2,4-diamine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

45 mg (0.17 mmol) of 4-[(3-ethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-fluoroaniline and 34 mg (0.17 mmol) of 4-chloro-6-trifluoromethyl)pyrimidine-2-amine are suspended in 5 ml of water. 24 μl of 37% strength hydrochloric acid are added, and the mixture is heated at reflux overnight. Another 70 mg (0.35 mmol) of 4-chloro-6-(trifluoromethyl)pyrimidine-2-amine and 40 μl of 37% strength hydrochloric acid are then added, and the mixture is heated at reflux for another night. Using 1N aqueous sodium hydroxide solution, the pH is then adjusted to 10. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:1 to 10:1). The product obtained is purified further by preparative HPLC.

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture is heated
  4. temperatureat reflux for another night
  5. concentrationThe mixture is concentrated under reduced pressure
  6. customthe residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:1 to 10:1)
  7. customThe product obtained
  8. customis purified further by preparative HPLC

출처 및 근거

ORD 기록
ord-5ea1cb1abebe4314b1481cb153e23b57
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329716B2

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