N-methyl-2-pyrrolidone → 4-(2,5-dimethylpyrimidin-4-yl)-N-(6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 60138노트

반응식

HRID 60138 반응식
CN1CCCC1=O.[CH3:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:23])[C:19]=2[C:20]([OH:22])=O)[C:12]([CH3:24])=[CH:11][N:10]=1.Cl.[F:26][C:27]1[C:28]([NH2:42])=[CH:29][C:30]2[N:31]([N:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:35]=2)[CH:32]=1.C(N(C(C)C)CC)(C)C>O>[CH3:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[N:17][N:18]([CH3:23])[C:19]=2[C:20]([NH:42][C:28]2[C:27]([F:26])=[CH:32][N:31]3[N:33]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:35]=[C:30]3[CH:29]=2)=[O:22])[C:12]([CH3:24])=[CH:11][N:10]=1

참가 물질

6

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 903834284-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 1177765626-Fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine hydrochloride

생성물 1

HCID 903833524-(2,5-dimethylpyrimidin-4-yl)-N-(6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

An N-methylpyrrolidone (7.7 ml) solution of the 4-(2,5-dimethylpyrimidin-4-yl)-1-methyl-1H-pyrazole-5-carboxylic acid (715 mg) obtained in (Example 3.22) <Step 2>, 6-fluoro-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine hydrochloride (obtained according to the method described in International Publication No. WO2012/076430, p. 80, Example 30-h) (815 mg), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate methanaminium (2.34 g), and diisopropylethylamine (2.69 ml) was stirred at 80° C. for 3 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. Organic layers were combined, and the combined organic layer was then dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (NH silica gel:eluent; heptane:ethyl acetate=3:1-1:1). The obtained fraction was concentrated under reduced pressure. The obtained residue (solid) was triturated with methanol to obtain the title compound (377 mg) in the form of a colorless solid.

후처리

  1. customobtained
  2. extractionthe mixed solution was then extracted with ethyl acetate
  3. dry with materialthe combined organic layer was then dried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was then purified by silica gel column chromatography (NH silica gel:eluent; heptane:ethyl acetate=3:1-1:1)
  6. concentrationThe obtained fraction was concentrated under reduced pressure
  7. customThe obtained residue (solid) was triturated with methanol

출처 및 근거

ORD 기록
ord-e9dabaa7eef544708a70151d9edca46e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440970B2

반응 노트

불러오는 중…