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

HRID 249868

Reaction equation

HRID 249868 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e86c045249124794b183b9a2113338c4
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Linked notes

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