HCID 86702335, compound → HCID 86702334, compound

HRID 2279080Notes

Reaction equation

HRID 2279080 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[C:13]([NH:20][C@H:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH3:22])[N:12]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1>C(OCC)(=O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([NH:20][C@H:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=3)[CH3:22])[N:12]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86702335HCID 86702335, compound

Product 1

HCID 86702334HCID 86702334, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N2-(5-chloro-2-methoxypyridin-3-yl)-N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitropyridine-2,6-diamine (Preparation 24b, 160 mg, 0.38 mmol) in ethyl acetate (11 mL) was hydrogenated using a H-Cube® Continuous-flow hydrogenation reactor and a Raney®-Nickel catalyst cartridge under a 80 bar pressure (flow=0.3 ml/min). Solvent was then concentrated to dryness under reduced pressure to yield the title compound (100 mg, 64%) as a green oil which was used in the next synthetic step without further purification.

Workup

  1. concentrationSolvent was then concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0ce3453ab6bc42ce9569a57b538031cc
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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