HCID 86702338, compound → HCID 86702337, compound

HRID 2279082Notes

Reaction equation

HRID 2279082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C@H:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)[CH3:19])[C:14]([CH3:27])=[CH:13][C:12]=2[N+:28]([O-])=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:12]([NH2:28])=[CH:13][C:14]([CH3:27])=[C:15]([NH:17][C@H:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=3)[CH3:19])[N:16]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86702338HCID 86702338, compound

Product 1

HCID 86702337HCID 86702337, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney®-Nickel (0.7 g) was added to a solution of N6-(5-chloro-2-methoxypyridin-3-yl)-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-methyl-5-nitropyridine-2,6-diamine (Preparation 25b, 0.67 g, 1.56 mmol) in ethanol (15 mL) and the resulting mixture was stirred at ambient temperature for 2 hours under a hydrogen atmosphere. The mixture was then filtered through Celite® and the filter cake was washed with methanol (30 mL). The combined filtrate and washings containing the title compound as a methanolic solution were concentrated under reduced pressure to half of their volume and were used in the next synthetic step without further purification.

Workup

  1. filtrationThe mixture was then filtered through Celite®
  2. washthe filter cake was washed with methanol (30 mL)
  3. additionThe combined filtrate and washings containing the title compound as a methanolic solution
  4. concentrationwere concentrated under reduced pressure to half of their volume
  5. customwere used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-14f495d4c8bd409c935ba92d21b7e5ce
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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