HCID 58484970, compound → HCID 86658722, compound

HRID 1255443Notes

Reaction equation

HRID 1255443 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([C@@H:16]2[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17]2)[C@H:9]([CH2:14][CH3:15])[C:10](OC)=[O:11])[C:5]([N+:23]([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:23][C:10](=[O:11])[C@@H:9]([CH2:14][CH3:15])[N:8]([C@@H:16]3[CH2:20][CH2:19][C:18]([F:22])([F:21])[CH2:17]3)[C:6]=2[N:7]=1

Participants

4

Reactant 1

HCID 58484970HCID 58484970, compound

Product 1

HCID 86658722HCID 86658722, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)((R)-3,3-difluorocyclopentyl)amino)butanoate (677 mg, 1.787 mmol) and iron powder (179.7 mg, 3.217 mmol) in glacial acetic acid (8 mL) was heated to 70° C. for 1 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 path of silica gel rinsing with more methanol-dichloromethane solution. The mother liquors were concentrated in vacuo. The residue was triturated with ethanol and the solid was filtered to afford the desired compound as white solid (348 mg, 61% 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 path of silica gel rinsing with more methanol-dichloromethane solution
  5. concentrationThe mother liquors were concentrated in vacuo
  6. customThe residue was triturated with ethanol
  7. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-4f274515162c4428b6ec79b1684097d5
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

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