Methyl 4,6-dichloropyridazine-3-carboxylate → Methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate

HRID 1396346Notes

Reaction equation

HRID 1396346 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH3:12])=[O:10].[CH:13]([C:16]1[N:21]=[C:20]([NH2:22])[CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14]>C(#N)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]([O:11][CH3:12])=[O:10])=[C:2]([NH:22][C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:13]([CH3:15])[CH3:14])[N:21]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylateHCID 217255966-(Propan-2-yl)pyridin-2-amine

Product 1

HCID 86689716Methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of methyl 4,6-dichloropyridazine-3-carboxylate (255 mg, 1.23 mmol) and 6-isopropylpyridin-2-amine (252 mg, 1.85 mmol) in acetonitrile (8.0 mL) was heated at 140° C. for 21 h. After cooling to room temperature the reaction mixture was concentrated in vacuo, then the residue purified by chromatography (silica, 20-45 μm, 80 g, Thomson, 0 to 10% acetone in dichloromethane, 20 min) to give methyl 6-chloro-4-(6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (113 mg, 30%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.64 (br. s., 1H) 9.39 (s, 1H) 7.63 (t, J=7.83 Hz, 1H) 6.94 (d, J=7.58 Hz, 1H) 6.78 (d, J=8.08 Hz, 1H) 4.12 (s, 3H) 3.01-3.19 (m, 1H) 1.31-1.42 (m, 6H). LCMS (EI/CI) m/z: 307 [M+H].

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe residue purified by chromatography (silica, 20-45 μm, 80 g, Thomson, 0 to 10% acetone in dichloromethane, 20 min)

Sources & evidence

ORD record
ord-ad18e0a235e74c4d8a7bf8fb755ac804
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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