Toluene → HCID 58762517, compound

HRID 1453309Notes

Reaction equation

HRID 1453309 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][C:20]2([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[O:25][C:24](=[O:26])C(=[N+]=[N-])[C:22](=[O:29])[CH2:21]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].[C:35]1(C)C=CC=CC=1>C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[Cl:9][C:10]1[CH:11]=[C:12]([CH2:18][CH2:19][C:20]2([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[O:25][C:24](=[O:26])[C:1]([N:2]([CH3:35])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[C:22]([OH:29])[CH2:21]2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7515N-MethylanilineHCID 58762625HCID 58762625, compound

Product 1

HCID 58762517HCID 58762517, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 21674Acetic acid, rhodium(2+) saltCatalyst

Procedure

To a refluxing solution of N-methylaniline (0.115 mL, 1.1 mmol) and rhodium (II) acetate (9.4 mg) in toluene (1.6 mL) was added 6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-3-diazo-dihydro-pyran-2,4-dione (0.080 g, 0.213 mmol) from Step 1 below over 1Hour. The reaction was stirred at reflux for three more hours. The reaction was concentrated by rotary evaporation, and then purified by preparatory HPLC to give the desired product (28 mg, 29% yield). 1H NMR (CDCl3) δ: 1.48-1.78 (m, 8H), 1.92-2.07 (m, 2H), 2.38 (p, J=8.10 Hz, 1H), 2.51-2.63 (m, 3H), 2.90 (d, J=17.90 Hz, 1H), 3.10 (s, 3H), 3.82 (s, 3H), 6.77-6.81 (m, 2H), 6.86 (t, J=7.44 Hz, 1H), 6.94 (dd, J1=8.38 Hz, J2=1.98 Hz, 1H), 7.10 (d, J=2.07 Hz), 7.18-7.23 (m, 2H), 7.29 (s, 1H).

Workup

  1. temperatureat reflux for three more hours
  2. concentrationThe reaction was concentrated by rotary evaporation
  3. custompurified by preparatory HPLC

Sources & evidence

ORD record
ord-c9fca41c5fc3491292e75e9c16e8f53f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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