Ethyl Acetate → HCID 68291139, compound

HRID 1408991Notes

Reaction equation

HRID 1408991 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9]([S:10][CH2:11][CH3:12])=[C:8]([C:13]([NH2:15])=[O:14])[CH:7]=[N:6][N:5]2[CH:16]=1.[Cu][C:18]#[N:19].CCOC(C)=O>CN1C(=O)CCC1>[C:18]([C:2]1[CH:3]=[C:4]2[C:9]([S:10][CH2:11][CH3:12])=[C:8]([C:13]([NH2:15])=[O:14])[CH:7]=[N:6][N:5]2[CH:16]=1)#[N:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 68291682HCID 68291682, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68291139HCID 68291139, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 6-bromo-4-(ethylthio)pyrrolo[1,2-b]pyridazine-3-carboxamide (200 mg, 0.666 mmol) and copper(I) cyanide (119 mg, 1.333 mmol) in NMP (3 mL) was heated to 180° C. for 1.5 hrs, and then 200° C. for 1.5 hrs under microwave oven (CEM). To the reaction mixture was added 50 mL of EtOAc. The mixture was washed with 30 mL of 10% LiCl solution, 30 mL of saturated NH4Cl solution, and 30 mL of brine and dried over Na2SO4. Filtration and concentration yielded 6-cyano-4-(ethylthio)pyrrolo[1,2-b]pyridazine-3-carboxamide (140 mg, 77% yield). MS (ES+) m/z: 247.08 (M+H); HPLC retention time: 1.902 min (analytical HPLC Method F).

Workup

  1. washThe mixture was washed with 30 mL of 10% LiCl solution, 30 mL of saturated NH4Cl solution, and 30 mL of brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-747db30059c04f3fa204eff5fc079f1d
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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