Tetrahydrofuran → tert-butyl-N-[1-[[6-ethynyl-5-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

HRID 535405ノート

反応式

HRID 535405 の反応式
[C:1]([O:5][C:6](=[O:42])[N:7]([CH3:41])[CH:8]([CH3:40])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]3=[N:20][C:19]=2[CH3:27])=[C:14]([C:28]#[C:29][Si](C(C)C)(C(C)C)C(C)C)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:42])[N:7]([CH:8]([CH3:40])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]3=[N:20][C:19]=2[CH3:27])=[C:14]([C:28]#[CH:29])[N:13]=1)=[O:10])[CH3:41])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86694388tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-tri-(propan-2-yl)silylethynyl]pyridin-2-yl]-amino]-1-oxopropan-2-yl]carbamate

生成物 1

HCID 86694391tert-butyl-N-[1-[[6-ethynyl-5-(2-methylimidazo[1,2-a]pyridin-3-yl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-tri-(propan-2-yl)silylethynyl]pyridin-2-yl]-amino]-1-oxopropan-2-yl]carbamate E1k (16.7 g, 28.3 mmol), THF (200 ml) and tetrabutylammonium fluoride (1 mol/l solution in THF, 34 ml, 34 mmol) is stirred at RT for 15 minutes. The mixture is diluted with DCM and extracted with a saturated aqueous solution of NaHCO3. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The mixture is concentrated in vacuo and the product purified by NP chromatography. Yield: 10.6 g (86%). HPLC-MS: M+H=434; tR=1.20 min (*Method—1).

後処理

  1. extractionextracted with a saturated aqueous solution of NaHCO3
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. concentrationThe mixture is concentrated in vacuo
  5. customthe product purified by NP chromatography

出典と根拠

ORDレコード
ord-b3989f568f5048eca9ff8e5716a86402
出典データセット
uspto-grants-2014_10
特許番号
US08859541B2

反応ノート

読み込み中…