2-Chloropyridin-4-amine → HCID 19082077, compound

HRID 963298Notes

Reaction equation

HRID 963298 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]([Cl:41])[CH:36]=1>ClCCl>[Cl:41][C:37]1[CH:36]=[C:35]([NH:34][C:17](=[O:19])[CH2:16][C:13]2[CH:12]=[CH:11][C:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:21])[F:20])=[CH:8][N:7]=3)=[CH:15][CH:14]=2)[CH:40]=[CH:39][N:38]=1

Participants

5

Reactant 3

HCID 844322-Chloropyridin-4-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19082076HCID 19082076, compound

Product 1

HCID 19082077HCID 19082077, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.3 g (7.78 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetic acid was dissolved in 10 ml of dichloromethane and cooled to a temperature of from -10° to 0° C. Then, 1.94 g (10.1 mmol) of 1-ethyl3-(dimethylaminopropyl)carbodiimide hydrochloride was added thereto, and the mixture was stirred at a temperature of from -10° to 0° C. 20 minutes later, 1.0 g (7.78 mmol) of 4-amino-2-chloropyridine was added thereto, and the mixture was gradually returned to room temperature with stirring and further stirred over night at room temperature. Then, 10 ml of dichloromethane was added to the reaction solution. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, dichloromethane was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 2.3 g of the desired product as a slightly yellow powder (melting point: 49 to 53° C.).

Workup

  1. temperaturecooled to a temperature of from -10° to 0° C
  2. customwas gradually returned to room temperature
  3. stirringwith stirring
  4. stirringfurther stirred over night at room temperature
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, dichloromethane was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b355543ec9ba457bab2a4e6596fbd825
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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