3-Methoxypropylamine → HCID 178495257, compound

HRID 506605Notes

Reaction equation

HRID 506605 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]>CN1C(=O)CCC1>[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 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-fec6a4f4998b4c299e485ecb3c0ac94a
Source dataset
uspto-grants-2010_08
Patent number
US07786113B2

Reaction notes

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