HCID 86730064, compound → HCID 86730065, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([NH:7][C:8]1[C:9]([NH:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[N:10][CH:11]=[CH:12][CH:13]=1)=O)[CH3:2]>C1(C)C=CC=CC=1>[CH:15]1([N:14]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[N:7]=[C:5]2[C:4]([O:3][CH2:1][CH3:2])=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of crude ethyl {[2-(cyclopentylamino)pyridin-3-yl]amino}(oxo)acetate (C6) (from the previous step, 2 g) in toluene (100 mL) was stirred at reflux for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified using silica gel chromatography (Gradient: 9% to 50% ethyl acetate in petroleum ether) to provide the product as a brown solid. Yield: 0.70 g, 2.7 mmol, 27% over 2 steps. 1H NMR (400 MHz, CD3OD) δ 8.53 (dd, J=4.6, 1.4 Hz, 1H), 8.14 (dd, J=8.2, 1.4 Hz, 1H), 7.40 (dd, J=8.2, 4.7 Hz, 1H), 5.79-5.89 (m, 1H), 4.51 (q, J=7.1 Hz, 2H), 2.48-2.61 (m, 2H), 2.07-2.20 (m, 4H), 1.70-1.83 (m, 2H), 1.46 (t, J=7.2 Hz, 3H).
Workup
- temperature