Benzoic Acid → HCID 68450074, 화합물

HRID 899961노트

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HRID 899961 반응식
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]([CH3:16])([CH3:15])[C:13]#N)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(O)(=[O:24])C1C=CC=CC=1.[F:26][C:27]([F:39])([F:38])[S:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1>ClC1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[C:6]([N:11]3[C:12]([CH3:16])([CH3:15])[C:13](=[O:24])[N:35]([C:32]4[CH:31]=[CH:30][C:29]([S:28][C:27]([F:38])([F:26])[F:39])=[CH:34][CH:33]=4)[C:36]3=[O:37])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

참가 물질

5

반응물 3

HCID 243Benzoic AcidHCID 27333921-Isocyanato-4-[(trifluoromethyl)sulfanyl]benzeneHCID 684491322-(Isoquinolin-5-ylamino)-2-methylpropionitrile

생성물 1

HCID 68450074HCID 68450074, 화합물수율 677.5%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
40 °C

실험 절차

500 mg (2.4 mmol) of 2-(isoquinolin-5-ylamino)-2-methylpropionitrile, 1.6 mg (0.013 mmol) of benzoic acid and 526 mg (2.4 mmol) of 4-(trifluoromethylthio)phenyl isocyanate in 4 ml of chlorobenzene were refluxed for 2 days. The resulting mixture was filtered and the filtrate was evaporated to dryness. The intermediate imine was separated out by preparative HPLC chromatography (RP 18, acetonitrile, water, 0.01% TFA). 60 mg of the resulting product were stirred for 1 hour at 40° C. with 1N hydrochloric acid. The solvent was evaporated off and the residue was taken up in sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases were dried and the residue remaining after evaporation was purified by flash chromatography (SiO2, methylene chloride/methanol=98/2), to give 38 mg of the desired product.

후처리

  1. filtrationThe resulting mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customThe intermediate imine was separated out by preparative HPLC chromatography (RP 18, acetonitrile, water, 0.01% TFA)
  4. customThe solvent was evaporated off
  5. extractionextracted with ethyl acetate
  6. customThe combined organic phases were dried
  7. customafter evaporation
  8. customwas purified by flash chromatography (SiO2, methylene chloride/methanol=98/2)

출처 및 근거

ORD 기록
ord-84fd2a0ed0274b55b2a3fe0e3a8042d4
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354933B2

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