4-Pyridinemethanamine → HCID 22249473, compound

HRID 1815181Notes

Reaction equation

HRID 1815181 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-cd13b30e3198458784504cda5b0616c3
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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