Ammonia → HCID 22172705, compound

HRID 2057019Notes

Reaction equation

HRID 2057019 reaction equation
Cl.[C:2]1([CH2:8][NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[N:13]=[CH:12][C:11]=2[NH:20][C:21](=O)[CH2:22][O:23][CH2:24][CH3:25])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>CO>[CH2:24]([O:23][CH2:22][C:21]1[N:9]([CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:20]=1)[CH3:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22172665HCID 22172665, compound

Product 1

HCID 22172705HCID 22172705, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

N-(4-Phenylmethylamino[1,5]naphthyridin-3-yl)-ethoxyacetamide hydrochloride (5.8 g, 15.5 mmol) was combined with a 7% solution of ammonia in methanol (100 mL), placed in a sealed Parr vessel and then heated at 150° C. for 6 hours. The reaction mixture was concentrated under vacuum. The residue was partitioned between water and dichloromethane. The dichloromethane layer was separated, washed with water, dried over magnesium sulfate and then concentrated under vacuum. The residue was recrystallized from methyl acetate to provide 4.3 g of 2-ethoxymethyl-1-phenylmethyl-1H-imidazo[4,5-c][1,5]naphthyridine, m.p. 118-119° C. Analysis: Calculated for C19H18N4O: % C, 71.68; % H, 5.70; % N, 17.60; Found: % C, 71.44; % H, 5.60; % N, 17.66.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between water and dichloromethane
  3. customThe dichloromethane layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was recrystallized from methyl acetate

Sources & evidence

ORD record
ord-5478a5a2651840d389dde4d5a85cc358
Source dataset
uspto-grants-2008_02
Patent number
US07335773B2

Reaction notes

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