1,1-Dimethylethyl 4-[(5-cyclopropyl-3-fluoro-2-nitrophenyl)amino]-1-piperidinecarboxylate → 1,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidinecarboxylate

HRID 447777Notes

Reaction equation

HRID 447777 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([F:27])[C:7]([N+:24]([O-])=O)=[C:8]([NH:10][CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:9]=2)[CH2:3][CH2:2]1>CO.[Pd]>[NH2:24][C:7]1[C:6]([F:27])=[CH:5][C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:9][C:8]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 596832701,1-Dimethylethyl 4-[(5-cyclopropyl-3-fluoro-2-nitrophenyl)amino]-1-piperidinecarboxylate

Product 1

HCID 596832651,1-Dimethylethyl 4-[(2-amino-5-cyclopropyl-3-fluorophenyl)amino]-1-piperidinecarboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl 4-[(5-cyclopropyl-3-fluoro-2-nitrophenyl)amino]-1-piperidinecarboxylate (D26, 0.8 mmol, 300 mg) was dissolved in MeOH (15 ml) and it was reduced by THALIS H-CUBE apparatus (bought from Asynt) using a palladium cartridge. The process yielded 280 mgs of the title compound, complete conversion, M+-COOC(CH3)3=250.

Sources & evidence

ORD record
ord-ef0e03b27f0f441c96ba353c6aeeca7d
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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