HCID 58484971, compound → HCID 86658721, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH2:16][C:17]2([C:20]([O:22]C)=O)[CH2:19][CH2:18]2)[C@@H:9]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10]2)[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:20](=[O:22])[C:17]3([CH2:19][CH2:18]3)[CH2:16][N:8]([C@@H:9]3[CH2:13][CH2:12][C:11]([F:14])([F:15])[CH2:10]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 1-(((2-chloro-5-nitropyrimidin-4-yl)(3,3-difluorocyclopentyl)amino)methyl)cyclopropane-carboxylate (3.90 g, 9.98 mmol) and iron powder (1.143 g, 20.46 mmol) in glacial acetic acid (50 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 path of silica gel rinsing with more methanol-dichloromethane solution. The mother liquors were concentrated in vacuo. The residue was triturated with methanol and the solid was filtered to afford the desired compound as a light pink solid (1.953 g, 60% yield).
Workup
- filtrationThe reaction mixture was filtered hot
- washthe cake was further washed with acetic acid
- concentrationThe mother liquors were concentrated in vacuo
- filtrationfiltered through a path of silica gel rinsing with more methanol-dichloromethane solution
- concentrationThe mother liquors were concentrated in vacuo
- customThe residue was triturated with methanol
- filtrationthe solid was filtered
Sources & evidence
- ORD record
- ord-8aa528c3ad314d898a3ca8c0046cc67b
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461149B2
Reaction notes
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