Sodium Methoxide → HCID 15684617, compound

HRID 728173Notes

Reaction equation

C[O-].[Na+].[C:4]([NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[N:12]=1)(=[O:6])[CH3:5].Cl[CH2:19][C:20]1[N:21]=[C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]2[CH:29]=1>CN(C)C=O>[C:4]([NH:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([O:17][CH2:19][C:20]3[N:21]=[C:22]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]4[CH:29]=3)[CH:14]=[CH:13][C:11]=2[N:12]=1)(=[O:6])[CH3:5]

Participants

Conditions

Temperature: 50 °C

Procedure

Methanolic sodium methoxide (28 wt. %, 1.25 g) was added to a solution of 2-acetamido-6-hydroxybenzoxazole (1.25 g) and 2-chloromethyl-7-methylimidazo[1,2-a]pyridine (1.41 g) in N,N-dimethylformamide (25 ml). After the mixture was stirred at 50° C. for 17 hours, the solvent was evaporated in vacuo. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (62.5 g) by eluting with chloroform-methanol (50:1, V/V), and the product obtained was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-acetamido-6-[(7-methylimidazo[1,2-a]pyridin-2-yl)methoxy]benzoxazole (0.22 g).

Workup

customthe solvent was evaporated in vacuo
additionWater was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel (62.5 g)
washby eluting with chloroform-methanol (50:1, V/V)
customthe product obtained
customwas recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record: ord-47370fdb90934639814a449427f54e96
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047411

Reaction notes

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