3-Amino-1-propanol → HCID 25119826, compound

HRID 1893492Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]1[CH:13]=[CH:14][N:15]=[C:7]1[C:6](=O)[NH:5]2.C[Si](C)(C)N[Si](C)(C)C.S([O-])([O-])(=O)=O.[NH4+].[NH4+].[NH2:33][CH2:34][CH2:35][CH2:36][OH:37]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]1[CH:13]=[CH:14][N:15]=[C:7]1[C:6]([NH:33][CH2:34][CH2:35][CH2:36][OH:37])=[N:5]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 7,8-difluoroimidazo[1,2-a]quinoxalin-4(5H)-one (Eur. J. Med. Chem. 1998, 33, 943) (20 mg, 0.090 mmol), hexamethyldisilazane (66 μL, 0.31 mmol), ammonium sulphate (2.4 mg, 0.018 mmol) and 3-aminopropan-1-ol (34 μL, 0.45 mmol) was stirred under argon at 120° C. overnight. The reaction mixture was allowed to cool down to room temperature and the white residue was diluted in ethyl acetate and water. A white precipitate was filtered off and the filtrate was washed with brine. The organic phase was dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 90/10) to afford the title compound as white crystals (4.5 mg, 18%)

Workup

temperatureto cool down to room temperature
filtrationA white precipitate was filtered off
washthe filtrate was washed with brine
dry with materialThe organic phase was dried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 90/10)

Sources & evidence

ORD record: ord-cc008eeaf30f4831b47eb0b188144788
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513250B2

Reaction notes

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