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Dichloromethane → 6-[1-(3-Trifluoromethyl-benzyl)-piperidin-4-ylamino]-pyridazine-3-carbonitrile

HRID 1258156
Notes
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Reaction equation

HRID 1258156 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.C(N(C(C)C)CC)(C)C.ClCCl>C(#N)C.O>[F:26][C:11]([F:10])([F:27])[C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)[CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([NH:22][C:2]2[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=2)[CH2:20][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 128889291-{[3-(Trifluoromethyl)phenyl]methyl}piperidin-4-amineHCID 133828716-Chloropyridazine-3-carbonitrile

Product 1

HCID 249892006-[1-(3-Trifluoromethyl-benzyl)-piperidin-4-ylamino]-pyridazine-3-carbonitrileYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-chloro-pyridazine-3-carbonitrile (D4) (0.130 g, 0.931 mmol), 1-(3-trifluoromethyl-benzyl)-piperidin-4-ylamine (D6) (0.241 g, 0.931 mmol) and diisopropylethylamine (0.243 ml, 1.4 mmol) in acetonitrile (3 ml) was stirred at 120° C. for 30 min., under microwave irradiation (Biotage MW-oven). Dichloromethane and water were added, and then the mixture washed with a saturated solution of sodium carbonate. The organic phase was filtered over cotton and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; 0-2% ammonia in methanol (7M)/dichloromethane) to yield E16 (0.215 g, 64%) as a solid. C18H18F3N5 requires 361. Found 362 (MH+); mp: 170.3° C.

Workup

  1. washthe mixture washed with a saturated solution of sodium carbonate
  2. filtrationThe organic phase was filtered over cotton
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by column chromatography (silica gel; 0-2% ammonia in methanol (7M)/dichloromethane)

Sources & evidence

ORD record
ord-f1c8b74b93d24522ab353a550e988c22
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466153B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes