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 451542ノート

反応式

HRID 451542 の反応式
[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]

参加物

4

反応物 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、化合物

生成物 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-amine収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b235718d215c48ebbea6efc2dbe66130
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

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