Diisopropylethylamine → HCID 22181339, compound

HRID 1796463Notes

Reaction equation

HRID 1796463 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[CH3:18][N:19]([CH3:24])[CH2:20][CH:21]([NH2:23])[CH3:22].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:18][N:19]([CH3:24])[CH2:20][CH:21]([NH:23][C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:16][CH3:17])[CH2:1][CH3:2])=[O:15])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 22181339HCID 22181339, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.500 g, 2.08 mmol), N1,N1-dimethyl-1,2-propanediamine (0.636 g, 6.24 mmol), DIPEA (2.2 mL, 12.5 mmol) and DMF (12 mL) was stirred 4 hours at room temperature. The reaction was then concentrated in vacuo, the residue was dissolved in 2 N NaOH (30 mL) and extracted with CH2Cl2 (3×40 mL). The combined organic phases were washed with brine (10 mL) dried over MgSO4, filtered, and concentrated in vacuo. The crude reaction mixture was purified by silica gel column chromatography (100% CH2Cl2 to 5% MeOH/CH2Cl2) to provide the title compound (0.621 g, 93%) as a bright yellow solid. 1H-NMR (CDCl3): δ 8.33 (d, J=6.4 Hz, 1H), 8.27 (d, J=2.0 Hz, 1H), 7.55 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 6.91 (d, J=9.6 Hz, 1H), 3.79 (heptet, J=7.2 Hz, 1H), 3.45 (br d, J=5.2 Hz, 4H), 2.55 (dd, J=12.0 Hz, J=7.6 Hz, 1H), 2.39 (dd, J=12.4 Hz, J=5.8 Hz, 1H), 2.29 (s, 6H), 1.69 (br s, 1H), 1.31 (d, J=6.8 Hz, 2H), 1.22 (t, J=7.4 Hz, 6H). MS (ESI) (M+H)+=323.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in 2 N NaOH (30 mL)
  3. extractionextracted with CH2Cl2 (3×40 mL)
  4. washThe combined organic phases were washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude reaction mixture
  9. customwas purified by silica gel column chromatography (100% CH2Cl2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0931b48641b942d2839dc246f127330b
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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