3-Chloroaniline → HCID 11558887, compound

HRID 550573Notes

Reaction equation

HRID 550573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C[Al](C)C.CCCCCCC.C[O:21][C:22]([C:24]1[C:29]([NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[N:28][CH:27]=[CH:26][N:25]=1)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:22]([C:24]2[C:29]([NH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)=[N:28][CH:27]=[CH:26][N:25]=2)=[O:21])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 8900HeptaneHCID 16682925TrimethylaluminumHCID 67151979HCID 67151979, compound

Product 1

HCID 11558887HCID 11558887, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Chloroaniline (140 mg, 1.1 mmol) was dissolved in 4 mL dioxane and trimethylaluminium-solution 2M in heptane (0.55 mL, 1.1 mmol) was added. The solution was stirred for 1 hr at room temperature and 3-(pyridin-3-ylamino)-pyrazine-2-carboxylic acid methyl ester (127 mg, 0.55 mmol) was added. The reaction mixture was stirred for 2 hrs at 80° C., cooled and quenched with 0.5 mL water. Sodium sulfate was added, stirred for 10 minutes, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:2->0:100 gradient) and the desired product was obtained as a yellow solid (13 mg, 7.2%), MS: m/e=326.2 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred for 2 hrs at 80° C.
  2. temperaturecooled
  3. customquenched with 0.5 mL water
  4. additionSodium sulfate was added
  5. stirringstirred for 10 minutes
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:2->0:100 gradient)

Sources & evidence

ORD record
ord-6beeaaebdb2549e899f56c42345cb371
Source dataset
uspto-grants-2011_05
Patent number
US07947685B2

Reaction notes

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