Potassium Carbonate → tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57866ノート

反応式

HRID 57866 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([C:15]4[N:20]=[C:19]([N:21]5[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O-:30])=[O:29])[CH2:23][CH2:22]5)[CH:18]=[CH:17][CH:16]=4)[C:8]=3[CH:7]=2)[CH:3]=[N:2]1.Br[CH2:32][CH:33]1[CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:35]1([CH2:34][N:1]2[CH:5]=[C:4]([C:6]3[N:11]=[CH:10][C:9]4[CH:12]=[N:13][N:14]([C:15]5[N:20]=[C:19]([N:21]6[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:4]([CH3:6])([CH3:5])[CH3:3])=[O:29])[CH2:23][CH2:22]6)[CH:18]=[CH:17][CH:16]=5)[C:8]=4[CH:7]=3)[CH:3]=[N:2]2)[CH2:33][CH2:32]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 867070614-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

生成物 1

HCID 86707060tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate収率 180.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 4-(6-(6-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (200 mg, 0.43 mmol), (bromomethyl)cyclopropane (100 mg, 0.65 mmol), and K2CO3 (120 mg, 0.87 mmol) in DMF (10 mL) was stirred at room temperature for 18 hours. The reaction mixture was extracted with EtOAc (100 mL), washed with brine (50 mL), dried over MgSO4, and concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-(6-(6-(1-(cyclopropylmethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a white solid (200 mg, 89.6%). MS (ESI) m/z: 515 [M+H]+.

後処理

  1. extractionThe reaction mixture was extracted with EtOAc (100 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by silica gel chromatography
  6. washas eluting solvents

出典と根拠

ORDレコード
ord-51ed50cc1eec435c8aaa8fa7eb0269fe
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

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