2-Methoxyethylamine → HCID 118063410, compound

HRID 1487270Notes

Reaction equation

HRID 1487270 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16].C(N(CC)CC)C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN1C(=O)CCC1>[CH3:12][O:13][CH2:14][CH2:15][NH:16][C:6]1[CH:7]=[C:2]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:3]=[CH:4][C:5]=1[NH2:9]

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 8083MorpholineHCID 8471TriethylamineHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 118063410HCID 118063410, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

2,4-Dichloro-5-nitro-pyridine (500 mg; 2.46 mmol), 2-methoxyethylamine (225 n1; 2.46 mmol) and triethylamine (400 μl; 2.82 mmol) are suspended in 2.5 ml NMP and stirred for 1 h at 25° C. To this suspension morpholine (500 μl; 5.71 mmol) is added and the resulting mixture is stirred for 16 h at 50° C. The crude intermediate is purified using reversed phase chromatography (prep. HPLC1). This intermediate is dissolved in 30 ml THF and palladium on carbon is added. The reaction mixture is stirred for 3 h at 25° C. and 4 bar hydrogen pressure. The solid material is filtered off and the solvent is evaporated.

Workup

  1. stirringthe resulting mixture is stirred for 16 h at 50° C
  2. customThe crude intermediate is purified
  3. dissolutionThis intermediate is dissolved in 30 ml THF
  4. additionpalladium on carbon is added
  5. stirringThe reaction mixture is stirred for 3 h at 25° C.
  6. filtrationThe solid material is filtered off
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-990ab8610e5a428cab889fb0c8c4571b
Source dataset
uspto-grants-2016_08
Patent number
US09428513B2

Reaction notes

Loading…