Triethylamine → 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoronicotinonitrile

HRID 75918

Reaction equation

HRID 75918 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH2:9])[CH:5]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[N:18]=[C:17](Cl)[C:16]([F:20])=[CH:15][C:12]=1[C:13]#[N:14].C(N(CC)CC)C>CC#N>[Cl:10][C:11]1[N:18]=[C:17]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)[C:16]([F:20])=[CH:15][C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 866206022-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoronicotinonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
82 °C

Procedure

A solution of 5-cyclopropyl-1H-pyrazol-3-amine (1.9 g, 16.0 mmol) in CH3CN (20 ml) was added dropwise to a solution of 2,6-dichloro-5-fluoronicotinonitrile (3.0 g, 16.0 mmol) and triethylamine (2.1 g, 20.0 mmol) in CH3CN (80 ml) at 25° C. The resulting solution was then heated to 82° C. for 18 hrs, and then cooled to 25° C., at which point the product precipitated from solution. The resulting solid was filtered, and washed with CH3CN (100 ml) to give the title compound (3.2 g, 73%). MS: Calcd.: 277. Found: [M+H]+ 278.

Workup

  1. temperaturecooled to 25° C., at which point the product
  2. customprecipitated from solution
  3. filtrationThe resulting solid was filtered
  4. washwashed with CH3CN (100 ml)

Sources & evidence

ORD record
ord-d477f2d67dd042bbaa2cb21266ee55a9
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Linked notes

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