6-tert-Butylpyridin-2-amine → HCID 86689772, compound

HRID 1396424Notes

Reaction equation

HRID 1396424 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].[C:14]([C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>C(#N)C>[C:14]([C:18]1[N:23]=[C:22]([NH:24][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:21]=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 134946346-tert-Butylpyridin-2-amineHCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689772HCID 86689772, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 4,6-dichloropyridazine-3-carboxylate (0.73 g, 3.3 mmol) and 6-tert-butylpyridin-2-amine (992 mg, 6.61 mmol, available commercially from J&W PharmLab, LLC) was dissolved in acetonitrile (3.00 mL) and heated at 130° C. for 20 h. After cooling to room temperature, the mixture was concentrated and the residue purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco) eluting with 0 to 20% acetone in dichloromethane over 20 min to give ethyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (539 mg, 48.7% yield) as a light brown residue. 1H NMR (CHLOROFORM-d) δ: 10.59 (s, 1H), 9.32 (s, 1H), 7.55 (t, J=7.9 Hz, 1H), 6.98 (d, J=7.2 Hz, 1H), 6.66 (d, J=7.9 Hz, 1H), 4.48 (q, J=7.2 Hz, 2H), 1.43 (t, J=7.2 Hz, 3H), 1.28-1.35 (m, 9H); LC-MS 335.0, 337.0 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. customthe residue purified by flash chromatography (spherical silica 20-45 μM, 50 g, Versaflash Supelco)
  4. washeluting with 0 to 20% acetone in dichloromethane over 20 min

Sources & evidence

ORD record
ord-94625553f0534908b6a9fbb70b0f540a
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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