Dimethylformamide → HCID 59349586, compound

HRID 415078Notes

Reaction equation

HRID 415078 reaction equation
[F:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][N:13]([CH:15]=O)[CH3:14].CN([C:20]([O:24]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN([CH:47]([CH3:49])[CH3:48])C(C)C>C(OCC)(=O)C>[F:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:20]([CH:49]1[CH2:47][CH2:48][CH2:14][N:13]([CH3:12])[CH2:15]1)=[O:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 888852-Fluoro-3-nitroanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59349586HCID 59349586, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL flask was charged with 2-fluoro-3-nitroaniline (19.108 mmol, commercially available from Aldrich), DMF (50 mL), HATU (26.05 mmol) and DIEA (52.11 mmol) and stirred at room temperature over night. The reaction mixture was diluted with ethyl acetate and washed with 10% lithium chloride solution (3×), 2 M sodium chloride (3×), dried over anhydrous sodium sulfate, filtered and the solvent was removed using the rotary evaporator under reduced pressure to yield N-(2-fluoro-3-nitrophenyl)-1-methylpiperidine-3-carboxamide which was used in the next step without further purification. MS (EI): 282 (MH+).

Workup

  1. washwashed with 10% lithium chloride solution (3×), 2 M sodium chloride (3×)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customthe rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-d63ab8e17b6e4e2e9190693b42c35700
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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