4-Pyridinemethanamine → HCID 22249473, compound

HRID 238487Notes

Reaction equation

HRID 238487 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:20][CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1>C(Cl)Cl>[ClH:1].[CH:17]([C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8]([C:7]2[C:2]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])=[CH:12][CH:13]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 773658HCID 773658, compound

Product 1

HCID 22249473HCID 22249473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (2-chloro(3-pyridyl))-N-(4-isopropylphenyl)carboxamide (1.5 g, from Step A) and 4-aminomethylpyridine (0.71 ml) was heated at 130° C. neat for 3 h. The reaction was cooled and diluted with CH2Cl2 and washed with H2O twice followed by brine. The organic layer was dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography with EtOAc and further mixed with MeOH and 1 N HCl/Et2O (2 ml). The solution was evaporated to furnish the titled compound. MS (ES+): 347 (M+H)+; (ES−): 345 (M−H). Calc'd. for C21H22N4O—346.18.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography with EtOAc
  6. additionfurther mixed with MeOH and 1 N HCl/Et2O (2 ml)
  7. customThe solution was evaporated

Sources & evidence

ORD record
ord-83d56be5d15a44bda2e29c3d21bf0aa4
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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