HCID 90403273, compound → HCID 90403180, compound

HRID 2279012Notes

Reaction equation

HRID 2279012 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[C:18]([O:20][C:21]4[C:22]([CH3:30])=[N:23][C:24]([N+:27]([O-])=O)=[CH:25][CH:26]=4)[CH:17]=[CH:16][N:15]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:30][C:22]1[N:23]=[C:24]([NH2:27])[CH:25]=[CH:26][C:21]=1[O:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[CH:13][CH:12]=2)[CH:19]=1

Participants

4

Reactant 1

HCID 90403273HCID 90403273, compound

Product 1

HCID 90403180HCID 90403180, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-4-(4-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)phenyl)piperazine (0.333 g, 0.821 mmol) in MeOH (20 mL) was treated with 10% Pd/C (50% w/w water, 0.087 g, 0.082 mmol) and hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness to afford 6-methyl-5-((2-(4-(4-methylpiperazin-1-yl)phenyl)pyridin-4-yl)oxy)pyridin-2-amine (247 mg, 80%). 1H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J=5.7 Hz, 1 H), 7.85 (d, J=8.8 Hz, 2 H), 7.21-7.20 (m, 2 H), 6.98 (d, J=8.8 Hz, 2 H), 6.57 (dd, J=5.6, 2.4 Hz, 1 H), 6.35 (d, J=8.7 Hz, 1 H), 5.94 (s, 2 H), 3.20 (t, J=4.7 Hz, 4 H), 2.45 (s, 4H), 2.22 (s, 3 H), 2.07 (s, 3H); MS (ESI) m/z: 376.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-206a163f19414bd1878ca3c80a9a95cf
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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