HCID 86702330, compound → HCID 86702331, compound

HRID 2279075Notes

Reaction equation

HRID 2279075 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=3)[C:14]([N+:26]([O-])=O)=[CH:13][CH:12]=2)[CH3:9])=[N:6][CH:7]=1>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=3)[C:14]([NH2:26])=[CH:13][CH:12]=2)[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86702330HCID 86702330, compound

Product 1

HCID 86702331HCID 86702331, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

N6-[(1S)-1-(5-Fluoropyridin-2-yl)ethyl]-N2-(2-methoxypyridin-3-yl)-3-nitropyridine-2,6-diamine (Preparation 22b, 131 mg, 0.34 mmol) was added to a suspension of palladium on carbon (10%, 18 mg) in ethanol (5 mL) and the reaction mixture was stirred at ambient temperature under a hydrogen atmosphere. After 7 hours, additional palladium on carbon was added (18 mg) and the reaction mixture was stirred at ambient temperature under a hydrogen atmosphere for further 15 hours. The mixture was then filtered through Celite® and the filter cake was washed with ethanol (5×10 mL). The combined filtrate and washings containing the title compound as a methanolic solution was used in the next synthetic step without further purification.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature under a hydrogen atmosphere for further 15 hours
  2. filtrationThe mixture was then filtered through Celite®
  3. washthe filter cake was washed with ethanol (5×10 mL)
  4. additionThe combined filtrate and washings containing the title compound as a methanolic solution
  5. customwas used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-43bada33ad7e4314b41376a19a6dabb4
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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