Diisopropylethylamine → 2,5-dichloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)nicotinonitrile

HRID 2189902Notes

Reaction equation

HRID 2189902 reaction equation
[Cl:1][C:2]1[N:9]=[C:8](Cl)[C:7]([Cl:11])=[CH:6][C:3]=1[C:4]#[N:5].CCN(C(C)C)C(C)C.[CH:21]1([C:24]2[NH:28][N:27]=[C:26]([NH2:29])[CH:25]=2)[CH2:23][CH2:22]1>CCCCO>[Cl:1][C:2]1[N:9]=[C:8]([NH:29][C:26]2[CH:25]=[C:24]([CH:21]3[CH2:23][CH2:22]3)[NH:28][N:27]=2)[C:7]([Cl:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 229063392,5,6-Trichloronicotinonitrile

Product 1

HCID 866206072,5-dichloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)nicotinonitrileYield 43.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,5,6-trichloronicotinonitrile (Method 44, 1.0 g, 4.8 mmol) and DIEA (0.81 g, 6.2 mmol) in n-BuOH (5 ml) was added 5-cyclopropyl-1H-pyrazol-3-amine (2.3 g, 19.3 mmol). The reaction was heated to 60° C. for 2 hours, at which point the reaction was cooled to room temperature and concentrated. The resulting residue was diluted with 10 ml ACN, and stored at 0° C. for 1 hour. The solids that formed were then filtered, washed with cold ACN, dried and collected to give the title compound (0.62 g, 43%). MS: Calcd.: 294. Found: [M+H]+ 295.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. additionThe resulting residue was diluted with 10 ml ACN
  4. customThe solids that formed
  5. filtrationwere then filtered
  6. washwashed with cold ACN
  7. customdried
  8. customcollected

Sources & evidence

ORD record
ord-9761b9bf6bed4c98a4885ee67e301ab4
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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