Sodium Bicarbonate → HCID 86652268、化合物

HRID 1409127ノート

反応式

HRID 1409127 の反応式
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.[N:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][CH:20]2[C:22](Cl)=[O:23])=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:22]([C@@H:20]2[CH2:21][C@H:19]2[C:16]2[CH:15]=[CH:14][N:13]=[CH:18][CH:17]=2)=[O:23])[CH:3]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amineHCID 767027172-(Pyridin-4-yl)cyclopropanecarbonyl chloride

生成物 1

HCID 86652268HCID 86652268、化合物収率 62.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

In a 100 mL round-bottomed flask was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 2.74 g, 15.02 mmol) in pyridine (75 ml) to give a yellow solution. Then, at 0° C., 2-(pyridin-4-yl)cyclopropanecarbonyl chloride (7D, 0.19 g, 1.046 mmol) in pyridine (1 ml) was added to give a suspension. After the reaction was complete, saturated NaHCO3 solution was added and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica using 20% MeOH/CH2Cl2 to provide trans-N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide (7E, 213 mg, 4% for 3 steps) as a yellow solid. 1H NMR (DMSO-d6) δ: 11.43 (s, 1H), 8.46 (d, J=6.1 Hz, 2H), 7.97 (s, 1H), 7.15-7.27 (m, 2H), 6.40 (s, 1H), 2.39-2.46 (m, 4H), 2.28-2.35 (m, 1H), 1.46-1.67 (m, 2H). ESI-MS: m/z 328.0 (M+H)+.

後処理

  1. customto give a yellow solution
  2. customto give a suspension
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica using 20% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-823e81b1984c4226ae517037754ecb38
出典データセット
uspto-grants-2014_12
特許番号
US08921358B2

反応ノート

読み込み中…