Triethylamine → 6-[4-(4-Chloro-phthalazin-1-yl)-piperazin-1-yl]-nicotinonitrile

HRID 42203

Reaction equation

HRID 42203 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](Cl)=[N:18][N:17]=1.CCN(CC)CC.CN1C(=O)CCC1>O>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][N:8]=3)[CH2:6][CH2:5]2)=[N:18][N:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 784901,4-DichlorophthalazineHCID 27371846-(Piperazin-1-yl)pyridine-3-carbonitrile

Product 1

HCID 441863796-[4-(4-Chloro-phthalazin-1-yl)-piperazin-1-yl]-nicotinonitrileYield 51.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 100-mL round-bottom flask is added 6-piperazin-1-yl-nicotinonitrile (9.60 g, 50 mmol), 1,4-dichlorophthalazine (11.2 g, 55.1 mmol, 1.1 eq), Et3N (3.5 mL, 250 mmol, 5 eq.), and NMP (100 mL). The mixture is heated to 80° C. for 2.5 h. Upon cooling to room temperature, the reaction is poured into H2O (500 mL) and the precipitate isolated by filtration, rinsing with additional H2O. Crude material is purified by recrystallization (CH2Cl2:heptanes) to afford 8.96 g title compound as a beige solid.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe precipitate isolated by filtration
  3. washrinsing with additional H2O
  4. customCrude material is purified by recrystallization (CH2Cl2:heptanes)

Sources & evidence

ORD record
ord-69b2432fdf324f2db2ebb0d08d6fe53f
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Linked notes

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