4-Methoxybenzylamine → HCID 21106455, compound

HRID 1765054Notes

Reaction equation

HRID 1765054 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][C:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:9]2)[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1>CN1C(=O)CCC1>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][C:2]2[CH:7]=[C:6]([N:8]3[CH:12]=[N:11][C:10]([NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:9]3)[CH:5]=[CH:4][N:3]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 21106436HCID 21106436, compound

Product 1

HCID 21106455HCID 21106455, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

[1 g, 3.68 mMol] of [1-(2-Chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-yl]-phenyl-amine was dissolved in 14 mL of NMP with [2.4 mL, 2.52 g, 18.4 mMol] of p-methoxybenzylamine and heated 250 C. for 15 min (MW, 150 W). The solvent was removed in vacuo (Kugel-Rohr style) and the residue was treated with MTBE. The ether was decanted away from the dark residue and was replaced with fresh MTBE and mass broken up with vigorous stirring. The ether was again decanted away and replaced with methanol and vigorously stirred for 1 hour. The tan solid was isolated via suction filtration and washed sequentially with methanol and MTBE. The resulting powder was boiled in hot acetonitrile for several minutes, allowed to cool, isolated via suction filtration, and washed with more acetonitrile and finally MTBE. Yield: 0.5g (38.5%). 1H NMR 500 MHz (DMSO-d6) ∂ 3.7(s, 3H), 4.45(d, 2H), 6.85(m, 3H), 6.93(s, 1H), 6.98(d, 1H), 0.3(m, 5H), 7.64(d, 2H), 8.05(d, 1H), 9.1(s, 1H), 9.5(s ex, H). LC/MS [M+H+]=373.

Workup

  1. temperatureheated 250 C
  2. customThe solvent was removed in vacuo (Kugel-Rohr style)
  3. additionthe residue was treated with MTBE
  4. customThe ether was decanted away from the dark residue
  5. customThe ether was again decanted away
  6. customThe tan solid was isolated via suction filtration
  7. washwashed sequentially with methanol and MTBE
  8. waitThe resulting powder was boiled in hot acetonitrile for several minutes
  9. temperatureto cool
  10. customisolated via suction filtration
  11. washwashed with more acetonitrile and finally MTBE

Sources & evidence

ORD record
ord-4c58c0e45a05457fa7230c0711da752b
Source dataset
uspto-grants-2007_06
Patent number
US07226920B2

Reaction notes

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