Ethyl 4,6-dichloropyridazine-3-carboxylate → HCID 86689797, compound

HRID 1396463Notes

Reaction equation

HRID 1396463 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[NH2:14][C:15]1[N:20]=[C:19]([C:21]([OH:24])([CH3:23])[CH3:22])[CH:18]=[CH:17][CH:16]=1>C(#N)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:2]([NH:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C:21]([OH:24])([CH3:22])[CH3:23])[N:20]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 866897962-(6-aminopyridin-2-yl)propan-2-ol

Product 1

HCID 86689797HCID 86689797, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4,6-dichloropyridazine-3-carboxylate (0.45 g, 2.04 mmol) and 2-(6-aminopyridin-2-yl)propan-2-ol (620 mg, 4.07 mmol) was dissolved in acetonitrile (3.00 mL) and heated at 130° C. for 18 h. The mixture was cooled, concentrated, the residue was adsorbed on silica gel and purified by flash chromatography (silica gel 45 μM, 160 g, Thomson) eluting with 0 to 100% hexanes/ethyl acetate over 40 min, to yield ethyl 6-chloro-4-(6-(2-hydroxypropan-2-yl)pyridin-2-ylamino)pyridazine-3-carboxylate (405 mg, 59.1% yield). 1H NMR (CHLOROFORM-d) δ: 10.72 (s, 1H), 9.00 (s, 1H), 7.76 (t, J=7.9 Hz, 1H), 7.34 (d, J=7.9 Hz, 1H), 6.89 (d, J=7.9 Hz, 1H), 5.21 (br. s., 1H), 4.60 (q, J=7.2 Hz, 2H), 1.67 (s, 6H), 1.54 (t, J=7.9 Hz, 3H); LC-MS 337.0, 339.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. custompurified by flash chromatography (silica gel 45 μM, 160 g, Thomson)
  4. washeluting with 0 to 100% hexanes/ethyl acetate over 40 min

Sources & evidence

ORD record
ord-4c5e74e9d93948679fcb2a82339bf38f
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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