3,6-Dichloropyridazine → HCID 58190547, compound

HRID 1892412Notes

Reaction equation

HRID 1892412 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([CH3:17])[C:13]([NH:15][NH2:16])=O.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C(O)CCC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]2[N:15]([C:13]([CH:12]([C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)[CH3:17])=[N:20][N:21]=2)[N:16]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 58190553HCID 58190553, compound

Product 1

HCID 58190547HCID 58190547, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

A sealed tube was charged with 2-(7-fluoroquinolin-6-yl)propanehydrazide (11.4 g, 48.9 mmol), 3,6-dichloro-pyridazine (8.01 g, 53.8 mmol) and 190 mL of n-butanol. The mixture was heated at 140° C. for 12 h. After cooling, the solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient to afford the title compound (7.1 g, 44%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.95 (d, 1H), 8.49-8.46 (m, 2H), 7.96 (d, 1H), 7.84 (d, 1H), 7.58 (dd, 1H), 7.48 (dd, 1H), 5.17 (q, 1H), 1.88 (d, 3H). LCMS (method A): [MH]+=328, tR=5.00 min.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc/methanol gradient

Sources & evidence

ORD record
ord-6b760b061cee4484ba11732f04d752d1
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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