6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine → 6-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine

HRID 1869279Notes

Reaction equation

HRID 1869279 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:25]=[C:24]([NH2:26])[C:23]([N+:27]([O-])=O)=[CH:22][C:21]=4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[C:5]2[CH:36]=[CH:37][CH:38]=[CH:39][C:4]=2[N:3]=1.[H][H]>[Pd].CCO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[N:25]=[C:24]([NH2:26])[C:23]([NH2:27])=[CH:22][C:21]=4[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[C:5]2[CH:36]=[CH:37][CH:38]=[CH:39][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 579860756-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 579860706-(4-{[4-(2-methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-5-phenylpyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-(4-{[4-(2-Methyl-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl)-3-nitro-5-phenylpyridin-2-amine (4-3; 0.244 g, 0.470 mmol) and 300 mg 10% palladium on carbon was stirred in 10 ml EtOH. Hydrogenate under 1 atm of hydrogen for 1 h. The reaction was filtered through celite, washed with EtOH and concentrated to afford a yellow oil (4-4). 1H NMR (CDCl3) δ 7.70 (d, 1H, J=7.6 Hz), 7.62 (m, 1H), 7.36-7.20 (m, 9H), 7.10 (m, 2H), 7.03 (s, 1H), 4.22 (m, 1H), 3.67 (s, 2H), 2.61 (s overlapping with m, 5H), 2.27 (m, 2H), 1.87 (m, 2H).

Workup

  1. filtrationThe reaction was filtered through celite
  2. washwashed with EtOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-74400bbc93c64044bf8db0f2a5b89f60
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

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