Dimethylformamide → HCID 17783816, compound

HRID 2270543Notes

Reaction equation

HRID 2270543 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:32]1[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][CH:35]=[CH:34][N:33]=1.CN(C)C=O>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([NH:20][C:32]2[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][CH:35]=[CH:34][N:33]=2)[CH:21]=[CH:22][CH:23]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 18331424HCID 18331424, compound

Product 1

HCID 17783816HCID 17783816, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(di-(t-butoxycarbonyl)aminomethyl)aniline (1.50 g), triethylamine (2.0 ml), 2-chloro-3-nitropyridine (1.10 g) and anhydrous dimethylformamide (15 ml) was stirred at 60° C. for 20 h and, thereafter, ethyl acetate and water were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 1.42 g of the titled compound (yield, 69%).

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-168d0c064d974f2ea66d86688ee7fe4d
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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