Sodium hydride → methyl 2-(5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)benzoxazole-4-carboxylate

HRID 249868

反応式

HRID 249868 の反応式
[H-].[Na+].[N:3]1[CH:4]=[CH:5][N:6]2[CH2:11][CH2:10][NH:9][CH2:8][C:7]=12.Cl[C:13]1[O:14][C:15]2[C:16](=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][CH:21]=2)[N:17]=1>C1COCC1>[N:3]1[CH:4]=[CH:5][N:6]2[CH2:11][CH2:10][N:9]([C:13]3[O:14][C:15]4[C:16](=[C:18]([C:22]([O:24][CH3:25])=[O:23])[CH:19]=[CH:20][CH:21]=4)[N:17]=3)[CH2:8][C:7]=12

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazineHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

生成物 1

HCID 66874003methyl 2-(5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)benzoxazole-4-carboxylate収率 37.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of NaH (60% dispersion in mineral oil, 0.130 g, 3.25 mmol) in THF (10 mL) was added 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.33 g, 2.71 mmol) and the reaction mixture stirred for 10 min. Methyl 2-chlorobenzoxazole-4-carboxylate (478 mg, 2.26 mmol), in THF (10 mL) was added and the reaction mixture was allowed to stir at room temperature 17 h. The reaction mixture was quenched with CH3OH (3 mL), and adsorbed onto silica gel (2 g). The crude product was purified by column chromatography (silica gel, 0.5 to 10% CH3OH in CH2Cl2) to afford methyl 2-(5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)benzoxazole-4-carboxylate (251 mg, 37%) as an orange oil. 1H NMR and MS consistent.

後処理

  1. stirringto stir at room temperature 17 h
  2. customThe reaction mixture was quenched with CH3OH (3 mL)
  3. customThe crude product was purified by column chromatography (silica gel, 0.5 to 10% CH3OH in CH2Cl2)

出典と根拠

ORDレコード
ord-e86c045249124794b183b9a2113338c4
出典データセット
uspto-grants-2011_01
特許番号
US07863271B2

関連ノート

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