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

HRID 75942Notes

Reaction equation

HRID 75942 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-Trichloropyridine-3-carbonitrile

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-0f4408dae076415696368a072908eef3
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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