Dimethylformamide → 2,3-Dimethyl-8-(2-bromo-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427494Notes

Reaction equation

S(O)(=O)(=O)C.[NH2:6][C:7]1[C:8]2[N:9]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1.[Br:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:23]=1[CH2:24]Cl.C(N(C(C)C)CC)(C)C.CN(C)C=O>O.C(Cl)Cl>[CH3:19][C:17]1[N:18]=[C:8]2[C:7]([NH:6][CH2:24][C:23]3[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:22]=3[Br:21])=[CH:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][N:9]2[C:16]=1[CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate (1.0 g, 5.0 mmol), 2-bromo-6-methylbenzylchloride (45%)(3.0 g, 5.0 mmol) and diisopropylethylamin (2.2 g, 17 mmol) were added to dimethylformamide (50 ml) and stirred at 50° C. for 48 h. Methylene chloride and water were added to the reaction mixture, the organic layer was separated, washed with saturated sodium chloride, dried (Na2SO4) and evaporated under reduced pressure. Purification of the residue twice by column chromatography on silica gel using methylene chloride:methanol (10:1) and ethylacetate as eluent gave 0.18 g (1%) of the desired product.

Workup

customthe organic layer was separated
washwashed with saturated sodium chloride
dry with materialdried (Na2SO4)
customevaporated under reduced pressure
customPurification of the residue twice by column chromatography on silica gel

Sources & evidence

ORD record: ord-2e3679b0ebe64071937205063e296722
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313137B1

Reaction notes

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