Ethyl Acetate → HCID 68232206, compound

HRID 869188Notes

Reaction equation

HRID 869188 reaction equation
F[C:2]1[N:7]=[N:6][C:5]([N:8]([CH2:16][C:17]2([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:20][CH2:19][CH2:18]2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[C:28]([C:30]1[CH:34]=[CH:33][NH:32][CH:31]=1)#[N:29].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[C:28]([C:30]1[CH:34]=[CH:33][N:32]([C:2]2[N:7]=[N:6][C:5]([N:8]([CH2:16][C:17]3([C:21]4[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=4)[CH2:20][CH2:19][CH2:18]3)[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:4][CH:3]=2)[CH:31]=1)#[N:29]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5642063-CyanopyrroleHCID 68233117HCID 68233117, compound

Product 1

HCID 68232206HCID 68232206, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirring solution of t-butyl 6-fluoropyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (200 mg, 551 μmol) in DMF (2 mL) was added 3-cyanopyrrole (61 mg, 661 μmol) and potassium carbonate (152 mg, 1.1 mmol). The reaction was heated to 110° C. and stirred for 30 min. The reaction was then poured into ethyl acetate (100 mL), washed with water (3×25 mL), and the organic layer was separated, dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography (EtOAC/hexanes) to afford 130 mg of t-butyl 6-(3-cyano-1H-pyrrol-1-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate as a pale yellow solid.

Workup

  1. washwashed with water (3×25 mL)
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (EtOAC/hexanes)

Sources & evidence

ORD record
ord-873a47ea31a34db0b1bb73d4507b0868
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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