6-Amino-3-chloropyridazine → HCID 49839964, compound

HRID 1919131Notes

Reaction equation

HRID 1919131 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[C:9]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>>[NH2:8][C:5]1[N:6]=[N:7][C:2]([N:19]2[CH2:18][CH2:17][N:16]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:21][CH2:20]2)=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 49839964HCID 49839964, compoundYield 62.6%

Conditions

Temperature
140 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 6-chloropyridazin-3-amine (2.58 g, 20 mmol) and N-Boc-piperazine (22.3 g, 120 mmol). The reaction mixture was heated at 140° C. and stirred for 2 h. It was then cooled to room temperature and the resulting solid was washed with ethyl acetate (100 mL), and the resulting residue was purified by flash column chromatography eluting with 30:1 methylene chloride/methanol to afford 330a as a yellow solid (3.5 g, 60%). MS: [M+H]+ 280.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperatureIt was then cooled to room temperature
  3. washthe resulting solid was washed with ethyl acetate (100 mL)
  4. customthe resulting residue was purified by flash column chromatography
  5. washeluting with 30:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-74b940192350468983852e53d1bd85f5
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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