2-Pyridinemethanamine → HCID 19592563, compound

HRID 613516Notes

Reaction equation

HRID 613516 reaction equation
[C:1]([CH2:4][C:5]1[C:14]2[C:9](=[C:10]([NH:15][C:16](=[O:25])[C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[CH:26]=[CH2:27])(O)=[O:2].C(Cl)(=O)C(C)(C)C.[NH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1>C(N(CC)CC)C>[Cl:23][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:24])[C:17]=1[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][C:6]([CH:26]=[CH2:27])=[C:5]2[CH2:4][C:1](=[O:2])[NH:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1)=[O:25]

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 62493Pivaloyl chlorideHCID 19592572HCID 19592572, compound

Product 1

HCID 19592563HCID 19592563, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-carboxymethyl-8-(2,6-dichlorobenzoylamino)-3-vinylquinoline (190.1 mg) were added pivaloyl chloride (62.8 mg) and triethylamine (52.7 mg) at 0° C., and the mixture was stirred for 1 hour at the same temperature. To the mixture was added 2-aminomethylpyridine (154 mg) at 0° C., and the mixture was stirred for 30 minutes at the same temperature and for 1 hour at ambient temperature. The mixture was partitioned between dichloromethane and water. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (methanol-dichloromethane) to give 8-(2,6-dichlorobenzoylamino)-4-[(pyridin-2-ylmethyl)carbamoylmethyl]-3-vinylquinoline (34.4 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature and for 1 hour at ambient temperature
  2. customThe mixture was partitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (methanol-dichloromethane)

Sources & evidence

ORD record
ord-611257ce03574b44b10b61d59e513b98
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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