HCID 58317725、化合物 → Tert-butyl 4-[6-[6-(3-methylisothiazol-5-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

HRID 57833

反応式

HRID 57833 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[S:39][N:38]=[C:37]([CH3:40])[CH:36]=1)CCC>CN(C)C(=O)C>[CH3:40][C:37]1[CH:36]=[C:35]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:19][CH2:18]5)[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[S:39][N:38]=1

参加物

4

反応物 2

HCID 58317725HCID 58317725、化合物HCID 86707015Tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate

生成物 1

HCID 86707039Tert-butyl 4-[6-[6-(3-methylisothiazol-5-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate収率 47%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

A solution of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]piperazine-1-carboxylate (120 mg, 0.290 mmol) and palladium(0)tetrakis(triphenylphosphine) (34 mg, 0.0290 mmol) in N,N-dimethylacetamide 1.0 mL was added tributyl-(3-methylisothiazol-5-yl)stannane (224 mg, 0.579 mmol). The reaction mixture heated at 150° C. for 45 min in a microwave (Biotage Inc.). The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 20% EtOAc) to give tert-butyl 4-[6-[6-(3-methylisothiazol-5-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (65 mg) 47% yield:

後処理

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 20% EtOAc)

出典と根拠

ORDレコード
ord-88e799dd9e274416bd7ebab949252e32
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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