3-Methoxypropylamine → HCID 178495257, compound

HRID 1435592Notes

Reaction equation

HRID 1435592 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[NH:19][C:11]3=[N:12][CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][CH2:22][CH2:23][CH2:24][NH2:25]>CN1CCCC1=O>[CH3:20][O:21][CH2:22][CH2:23][CH2:24][NH:25][C:2]1[CH:7]=[C:6]([C:8]2[NH:19][C:11]3=[N:12][CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 16723-MethoxypropylamineHCID 178526789HCID 178526789, compound

Product 1

HCID 178495257HCID 178495257, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.20 g (4.35 mmol) 2-(2-Chloro-pyridin-4-yl)-6-nitro-3H-imidazo[4,5-b]pyridine in 12 ml dry N-methylpyrrolidone (NMP) and 1.18 g (13 mmol) 3-methoxypropylamine were heated to 200 C in a closed vessel in a microwave reactor for 30 min. The solvent was removed under vacuum and the residue dissolved in a mixture of 20 ml ethyl acetate and 30 ml 5% aqueous HCl. The HCl phase was separated and brought to alkaline pH by addition of conc. ammonia. The alkaline aqueous phase was extracted with dichloromethane, and the organic phases were combined and dried. Evaporation and chromatography of the residue on silica in ethyl acetate/methanol mixtures gave 480 mg of the title product.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in a mixture of 20 ml ethyl acetate and 30 ml 5% aqueous HCl
  3. customThe HCl phase was separated
  4. additionbrought to alkaline pH by addition of conc. ammonia
  5. extractionThe alkaline aqueous phase was extracted with dichloromethane
  6. customdried
  7. customEvaporation and chromatography of the residue on silica in ethyl acetate/methanol

Sources & evidence

ORD record
ord-c6c8135073c048d5a6af5f7ebcc666df
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

Loading…