Propylamine → HCID 86730389, compound

HRID 531220Notes

Reaction equation

HRID 531220 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[O:19][C:20]1[C:21]([F:42])=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([O:31]C1C=CC([N+]([O-])=O)=CC=1)=O)[C:24]([CH3:41])=[CH:23]2>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][N:11]=[C:10]2[O:19][C:20]1[C:21]([F:42])=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([NH:4][CH2:1][CH2:2][CH3:3])=[O:31])[C:24]([CH3:41])=[CH:23]2

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86730387HCID 86730387, compound

Product 1

HCID 86730389HCID 86730389, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Propylamine (210 μL, 2.55 mmol) was added to a solution of Compound 12 in dry N,N-dimethylformamide and the reaction stirred for 40 minutes. The solvent was removed by rotary evaporator and the crude residue suspended in saturated aqueous NaHCO3. Precipitate was filtered and washed with additional NaHCO3 (20 mL×2) and diethyl ether (20 mL). Solids were dissolved in a minimal amount of methylene chloride and precipitated from diethyl ether. Precipitate was filtered and purified by reverse phase HPLC to give 27 mg of Compound 13 (two-step yield=7%) as a tan solid. m/z 439.2 (M+H, 100%) (positive ionization mode). 1H-NMR (CDCl3, 400 MHz): δ 1.06 (3H, t); 1.74 (2H, m); 2.60 (3H, s); 4.08 (6H, d); 5.69 (1H, t); 6.47 (1H, s); 7.12 (1H, dd); 7.35 (1H, s); 7.48 (1H, d); 7.63 (1H, s); 8.61 (1H, s).

Workup

  1. customThe solvent was removed by rotary evaporator
  2. filtrationPrecipitate was filtered
  3. washwashed with additional NaHCO3 (20 mL×2) and diethyl ether (20 mL)
  4. dissolutionSolids were dissolved in a minimal amount of methylene chloride
  5. customprecipitated from diethyl ether
  6. filtrationPrecipitate was filtered
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-834253a2d96e44d39c541a0c8734c94f
Source dataset
uspto-grants-2016_05
Patent number
US09353123B2

Reaction notes

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