4-Pyridinemethanamine → HCID 23289847, compound

HRID 366790Notes

Reaction equation

HRID 366790 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21](SC)=[N:22][C:23]#[N:24])[CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(#N)C>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[N:29][CH2:30][C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)[NH:22][C:23]#[N:24])[CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 23289855HCID 23289855, compound

Product 1

HCID 23289847HCID 23289847, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-(8-chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-yl)-N-cyano-1-piperazinecarboximidothioate (200 mg, 0.465 mmol) was dissolved in acetonitrile (1 ml) in a 25 ml flask, and 4-aminomethylpyridine (0.94 ml, 9.30 mmol) was added. The mixture was refluxed for 1.6 hours. The reaction mixture was cooled and then acetonitrile was distilled off. The resulting tar was dissolved in water and CH2Cl2. The layers were separated; the aqueous layer was extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), filtered through `Celite` and concentrated. The residue was partially purified by flash chromatography, and the product (228 mg) was purified by further chromatography to afford the pure product (193 mg, 87%); MS (CI, M+H)=490.

Workup

  1. temperatureThe mixture was refluxed for 1.6 hours
  2. temperatureThe reaction mixture was cooled
  3. distillationacetonitrile was distilled off
  4. dissolutionThe resulting tar was dissolved in water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted three times with CH2Cl2
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered through `Celite` and
  10. concentrationconcentrated
  11. customThe residue was partially purified by flash chromatography
  12. customthe product (228 mg) was purified by further chromatography

Sources & evidence

ORD record
ord-dc4ee332f6cb460f81c32d8534719821
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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