HCID 86701071, compound → HCID 86701072, compound

HRID 334496Notes

Reaction equation

HRID 334496 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([N+:23]([O-])=O)[C:21]=2[NH2:22])[CH:5]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[CH:7]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:16]2[C:21]([NH2:22])=[C:20]([NH2:23])[CH:19]=[N:18][CH:17]=2)[CH:5]=[C:6]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)[CH:7]=1

Participants

4

Reactant 1

HCID 86701071HCID 86701071, compound

Product 1

HCID 86701072HCID 86701072, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(3-fluoro-5-((4-methylpiperazin-1-yl)methyl)phenyl)-5-nitropyridin-4-amine (CIV) (265 mg, 0.77 mmol) in MeOH (5 mL) was added 10% Pd/C (40 mg, 15% by wt). The solution was purged with hydrogen and stirred for 4 h at room temperature under hydrogen. The suspension was filtered through Celite and concentrated under vacuum to produce 5-(3-fluoro-5-((4-methylpiperazin-1-yl)methyl)phenyl)pyridine-3,4-diamine (CV) as a tan solid (210 mg, 0.66 mmol, 86% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 2.14 (s, 3H), 2.32-2.40 (m, 8H), 3.51 (s, 2H), 4.71 (brs, 2H), 5.05 (brs, 2H), 7.06-7.10 (m, 2H), 7.14 (s, 1H), 7.43 (s, 1H), 7.67 (s, 1H); ESIMS found C17H22FN5 m/z 316 (M+H).

Workup

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0395abfe7a774b2b9f26ac092c61ff23
Source dataset
uspto-grants-2014_11
Patent number
US08883822B2

Reaction notes

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