HCID 58484961, compound → HCID 86658720, compound

HRID 1255433Notes

Reaction equation

HRID 1255433 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]=1

Participants

4

Reactant 1

HCID 58484961HCID 58484961, compound

Product 1

HCID 86658720HCID 86658720, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

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).

Workup

  1. filtrationThe reaction mixture was filtered hot
  2. washthe cake was further washed with acetic acid
  3. concentrationThe mother liquors were concentrated in vacuo
  4. filtrationfiltered through a pad of silica gel rinsing with more methanol-dichloromethane solution
  5. concentrationThe filtrates were concentrated in vacuo
  6. customThe residue was triturated with methanol
  7. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-44bf04a187c64659bbdb7934cf76166f
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

Loading…