Triethylamine → HCID 67451790, compound

HRID 869148Notes

Reaction equation

HRID 869148 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]1[C:12]([C:17]2([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18]2)=[N:13][CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C.CN1C(=O)CCC1>O.C(OCC)(=O)C>[F:10][C:11]1[C:12]([C:17]2([CH2:21][NH:22][C:2]3[N:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=3)[CH2:20][CH2:19][CH2:18]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 133828716-Chloropyridazine-3-carbonitrileHCID 67453361HCID 67453361, compound

Product 1

HCID 67451790HCID 67451790, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a 20 dram vial was added 6-chloropyridazine-3-carbonitrile (1.0 g, 7.2 mmol, 1.0 equiv), (1-(3-fluoropyridin-2-yl)cyclobutyl)methanamine (1.36 g, 7.6 mmol, 1.05 equiv), triethylamine (2.1 mL, 14.4 mmol, 2.0 equiv), and NMP (2 mL). The reaction was heated at 130° C. for 12 h and then diluted with water (20 mL) and ethyl acetate (50 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer and then washed with brine (1×20 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography (20-30% EtOAc/hexanes) to give 507 mg (25%) of 6-((1-(3-fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazine-3-carbonitrile. m/z=284 [M+H]+.

Workup

  1. customAfter transferring to a separatory funnel
  2. customthe organic layer was separated from the aqueous layer
  3. washwashed with brine (1×20 mL)
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude solid that
  8. customwas purified by silica gel column chromatography (20-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cb797b31ac7f41d8befda098b63eb0d3
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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