Ammonia → HCID 67388746, compound

HRID 908486Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:15]([C:16]2[O:17][C:18]3[C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:14][CH:13]=[CH:12][N:11]=1.C(Cl)(Cl)Cl.N>O1CCCC1>[NH2:9][C:10]1[C:15]([C:16]2[O:17][C:18]3[C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[CH:14][C:13]([Br:1])=[CH:12][N:11]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1-bromopyrrolidine-2,5-dione (233 mg) was added to a stirred solution of methyl 2-(2-amino-3-pyridyl)-1,3-benzoxazole-7-carboxylate (335 mg) dissolved in tetrahydrofuran (10 ml) over a period of 5 minutes. The resulting solution was stirred at 25° C. for 2 hours. The solvent was evaporated and the mixture was washed with water and dried over phosphorus pentoxide under reduce pressure to afford a brown solid. The mixture was adsorbed on silica gel with chloroform and methanolic ammonia (7N). The crude product was purified by flash chromatography on silica gel eluting with 0 to 2% methanol in dichloromethane. The solvent was evaporated to dryness to afford methyl 2-(2-amino-5-bromo-3-pyridyl)-1,3-benzoxazole-7-carboxylate (405 mg) as a pale brown solid. NMR Spectrum: (DMSOd6) 3.99 (s, 3H), 7.56 (dd, 1H), 7.85 (bs, 2H), 7.97 (d, 1H), 8.12 (d, 1H), 8.29 (s, 1H), 8.35 (s, 1H); Mass spectrum: M+H+ 348-350.

Workup

customThe solvent was evaporated
washthe mixture was washed with water
dry with materialdried over phosphorus pentoxide
customto afford a brown solid
customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 2% methanol in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-f8523844e14f4164a12266bf4d4a666c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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