Trimethylsilyl cyanide → 4-(8-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1-(6-methylpyrimidin-4-yl)piperidine-4-carbonitrile

HRID 451537ノート

反応式

HRID 451537 の反応式
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:3]=1.[F:15][C:16]1[CH:17]=[C:18]([C:23]2[C:24]3[N:25]([N:29]=[C:30]([NH2:32])[N:31]=3)[CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:20][C:21]=1[F:22].C[Si]([C:37]#[N:38])(C)C>CC(O)=O>[F:15][C:16]1[CH:17]=[C:18]([C:23]2[C:24]3[N:25]([N:29]=[C:30]([NH:32][C:11]4([C:37]#[N:38])[CH2:12][CH2:13][N:8]([C:4]5[CH:3]=[C:2]([CH3:1])[N:7]=[CH:6][N:5]=5)[CH2:9][CH2:10]4)[N:31]=3)[CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:20][C:21]=1[F:22]

参加物

5

反応物 3

HCID 82115Trimethylsilyl cyanideHCID 61226887HCID 61226887、化合物HCID 673372048-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-A]pyridin-2-amine

生成物 1

HCID 583979704-(8-(3,4-Difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1-(6-methylpyrimidin-4-yl)piperidine-4-carbonitrile収率 9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 1-(6-methylpyrimidin-4-yl)piperidin-4-one (see example 93b, 100 mg, 0.523 mmol) and 8-(3,4-difluorophenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (129 mg, 0.523 mmol) in AcOH was added dropwise trimethylsilyl cyanide (196 μL, 1.57 mmol) and the resulting mixture stirred at room temperature for 88 hours. The mixture was then poured onto NaOH (6 M, 6 mL) and stirred for 10 minutes. The precipitate was then filtered off and dried. Purification by chromatography (silica gel, 20 g, 30 to 100% ethyl acetate in heptane) afforded the title compound (20 mg, 9%) as a yellow solid. MS ISP (m/e): 447.4 [(M+H)+].

後処理

  1. additionThe mixture was then poured onto NaOH (6 M, 6 mL)
  2. stirringstirred for 10 minutes
  3. filtrationThe precipitate was then filtered off
  4. customdried
  5. customPurification by chromatography (silica gel, 20 g, 30 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-a89d565b9d8c4b6299e58c537adc5465
出典データセット
uspto-grants-2013_07
特許番号
US08486967B2

反応ノート

読み込み中…