HCID 58484961, compound → HCID 86658720, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C@@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)[CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=O)[C:5]([N+:24]([O-])=O)=[CH:4][N:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:24][C:11](=[O:13])[C:10]([CH3:16])([CH3:15])[CH2:9][N:8]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:22])([F:23])[CH2:18]3)[C:6]=2[N:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A mixture of (R)-methyl 3-((2-chloro-5-nitropyrimidin-4-yl)(3,3-difluorocyclopentyl)amino)-2,2-dimethylpropanoate (2.74 g, 6.98 mmol) and iron powder (0.799 g, 14.31 mmol) in glacial acetic acid (30 mL) was heated to 70° C. for 2 hours. The reaction mixture was filtered hot and the cake was further washed with acetic acid. The mother liquors were concentrated in vacuo. The residue was taken up in a 15% solution of methanol in dichloromethane and filtered through a pad of silica gel rinsing with more methanol-dichloromethane solution. The filtrates were concentrated in vacuo. The residue was triturated with methanol and the solid was filtered to afford the title compound as an off-white solid (1.67 g, 72% yield).