2-Propanol, 1-amino-2-methyl- → 2-Methyl-1-(6-phenylethynyl-pyridazin-3-ylamino)-propan-2-ol

HRID 629244Notes

Reaction equation

HRID 629244 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.[NH2:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19]>N1C=CC=CC=1>[CH3:19][C:18]([OH:20])([CH3:21])[CH2:17][NH:16][C:2]1[N:3]=[N:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 951022-Propanol, 1-amino-2-methyl-HCID 126802603-Chloro-6-(phenylethynyl)pyridazine

Product 1

HCID 575167742-Methyl-1-(6-phenylethynyl-pyridazin-3-ylamino)-propan-2-olYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-chloro-6-(phenylethynyl)pyridazine (CAS 77778-15-5) (300 mg, 1.4 mmol) and 1-amino-2-methylpropan-2-ol (137 mg, 147 μl, 1.54 mmol, 1.1 equiv.) in 3 ml of pyridine was heated 20 hours at 120° C. in a sealed tube. The solvent was removed in vaccuo. The residue was taken up in ethyl acetate/methanol, adsorbed onto 4 g of silica and purified on a 20 g flash chromatography column using a heptane to ethyl acetate gradient to yield 90 mg (24% yield) of the title compound as a crystalline light yellow solid, MS: m/e=268.2 (M+H+).

Workup

  1. customThe solvent was removed in vaccuo
  2. custompurified on a 20 g flash chromatography column

Sources & evidence

ORD record
ord-431e903d5165433f89094c018ac8eee5
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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