Trifluoroacetic acid → N-(2-Aminophenyl)-7-methoxy-7-[4-(N,N-dimethylamino)phenyl]-2,4-heptadienamide

HRID 1182452Notes

Reaction equation

HRID 1182452 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH2:4][CH:5]=[CH:6][CH:7]=[CH:8][C:9]([OH:11])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]1([NH2:40])[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH2:39].FC(F)(F)C(O)=O>C1COCC1.C(OCC)(=O)C>[NH2:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[NH:40][C:9](=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH2:4][CH:3]([O:2][CH3:1])[C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7243O-PhenylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 724803387-Methoxy-7-[4-(N,N-dimethylamino)phenyl]-2,4-heptadienoic acid

Product 1

HCID 86585715N-(2-Aminophenyl)-7-methoxy-7-[4-(N,N-dimethylamino)phenyl]-2,4-heptadienamideYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of carboxylic acid 16 (207 mg, 0.753 mmol) in anhydrous THF (10 mL) was added 1,1′-carbonyldiimidazole (128 mg, 0.790 mmol) at rt, and the mixture was stirred overnight. To the resulting solution was added 1,2-phenylenediamine (570 mg, 5.27 mmol), followed by trifluoroacetic acid (52 μl ), and the reaction mixture was stirred for 16 h at rt. The reaction mixture was diluted with ethyl acetate (30 mL), washed with saturated NaHCO3 solution (5 mL) and then water (10 mL), dried (MgSO4), and concentrated. Purification by flash silica gel chromatography (50% ethyl acetate in toluene) afforded the title compound 20 (115 mg, 42% yield): 1H NMR (300 MHz, CDCl3) δ 7.44 (br. s, 1H), 7.01-7.29 (m, 5H), 6.70-6.78 (m, 4H), 6.09 (m, 2H), 5.90 (d, J=15.0 Hz, 1H), 4.10 (br. t, J=6.6 Hz, 1H), 3.89 (br. s, 2H), 3.18 (s, 3H), 2.95 (s, 3H), 2.66 (m, 1H), 2.50 (m, 1H); 13C NMR (75.4 MHz, CDCl3) δ 40.5, 41.6, 82.8, 112.3, 118.1, 119.4, 121.7, 124.4, 125.1, 127.0, 127.6, 128.6, 130.0, 140.0, 140.8, 142.5, 150.2, 164.7.

Workup

  1. stirringthe reaction mixture was stirred for 16 h at rt
  2. washwashed with saturated NaHCO3 solution (5 mL)
  3. dry with materialwater (10 mL), dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash silica gel chromatography (50% ethyl acetate in toluene)

Sources & evidence

ORD record
ord-d137d314f9764a3c9c483e121285fb45
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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