HCID 86698331, compound → HCID 86698332, compound

HRID 877134Notes

Reaction equation

HRID 877134 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH:14]=[C:15]([F:17])[CH:16]=1>CO.[Pd]>[CH3:22][N:21]([CH3:23])[CH2:20][CH2:19][NH:18][C:13]1[CH:12]=[C:11]([C:3]2[C:2]([NH2:1])=[C:7]([NH2:8])[CH:6]=[N:5][CH:4]=2)[CH:16]=[C:15]([F:17])[CH:14]=1

Participants

4

Reactant 1

HCID 86698331HCID 86698331, compound

Product 1

HCID 86698332HCID 86698332, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N1-(3-(4-amino-5-nitropyridin-3-yl)-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (LXXVII) (2.1 g, 6.58 mmol) in MeOH (40 mL) was added 10% Pd/C (300 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-(2-(dimethylamino)ethylamino)-5-fluorophenyl)pyridine-3,4-diamine (LXXVIII) as a brown solid (1.90 g, 6.57 mmol, 99.8% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 2.20 (s, 6H), 2.46 (t, J=7 Hz, 2H), 3.12 (q, J=6 Hz, 2H), 4.79 (s, 2H), 5.21 (s, 2H), 5.91 (t, J=5 Hz, 1H), 6.28 (dd, J=9 Hz, J=1 Hz, 1H), 6.36 (t, J=2 Hz, 1H), 6.37-6.42 (m, 1H), 7.46 (s, 1H), 7.64 (s, 1H); ESIMS found C15H20FN5 m/z 290.1 (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-3b99033b4d9f406daf406845ec5166dc
Source dataset
uspto-grants-2015_03
Patent number
US08987298B2

Reaction notes

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