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

HRID 1893492
Notes
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Reaction equation

HRID 1893492 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 90863-Amino-1-propanolHCID 13838HexamethyldisilazaneHCID 6097028Ammonium SulfateHCID 10632760HCID 10632760, compound

Product 1

HCID 25119826HCID 25119826, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

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

  1. temperatureto cool down to room temperature
  2. filtrationA white precipitate was filtered off
  3. washthe filtrate was washed with brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes