Triethylamine → HCID 178522056, 화합물

HRID 45814

반응식

HRID 45814 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1.C(N(CC)CC)C>N1C=CC=CC=1>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28]([NH:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:30])[F:31])=[CH:26][CH:25]=4)=[O:29])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 178507541HCID 178507541, 화합물

생성물 1

HCID 178522056HCID 178522056, 화합물수율 75%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

To 3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (700 mg, 3 mmol) in anhydrous pyridine (15 mL) at 0° C. 4-trifluoromethylphenylisocyanate (420 μL, 3 mmol) was added. The reaction was stirred for 2 hours at 0° C. under nitrogen atmosphere to give a mixture of monourea and bis-urea as regioisomeric mixture. Solvent was removed under reduced pressure. The residue was dissolved in methanol (15 mL) and triethylamine (1 mL, 7.8 mmol) was added and the reaction was stirred at room temperature overnight. After this time only the monourea could be detected by HPLC/MS. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (100 mL) and washed successively with water (3×50 mL). The crude was purified by silica gel column chromatography (DCM/methanol 9:1) to give the desired product as a white solid (75%).

후처리

  1. customat 0° C
  2. customto give
  3. customSolvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (15 mL)
  5. stirringthe reaction was stirred at room temperature overnight
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  8. washwashed successively with water (3×50 mL)
  9. customThe crude was purified by silica gel column chromatography (DCM/methanol 9:1)

출처 및 근거

ORD 기록
ord-568357e338334b369eb32b7a7405ce38
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541575B2

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