4-(8-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1-(6-methylpyrimidin-4-yl)piperidine-4-carbonitrile → 8-(3,4-Difluorophenyl)-N-(4-methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451542노트

반응식

HRID 451542 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4([C:32]#N)[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=5)[CH2:21][CH2:20]4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].C[Mg]Br>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4([CH3:32])[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27][N:26]=5)[CH2:21][CH2:20]4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

4

반응물 2

HCID 583979704-(8-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1-(6-methylpyrimidin-4-yl)piperidine-4-carbonitrileHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 583980568-(3,4-Difluorophenyl)-N-(4-methyl-1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine수율 19%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1-(6-methylpyrimidin-4-yl)piperidine-4-carbonitrile (Example 231) (50 mg, 112 μmol) in THF (2 mL) was added methylmagnesium bromide (1.4 M in toluene:THF, 240 μL, 336 μmol) dropwise at 0° C., and the resulting mixture was allowed to warm up to room temperature and stirred for 3 hours. Then the mixture was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 10 g, 0 to 10% methanol in dichloromethane) afforded the title compound (9 mg, 19%) as a light yellow solid.

후처리

  1. customThen the mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica gel, 10 g, 0 to 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-b235718d215c48ebbea6efc2dbe66130
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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