N-(3-Aminopropyl)morpholine → HCID 68650098, compound

HRID 1029119Notes

Reaction equation

HRID 1029119 reaction equation
Cl[C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[NH:16]C2C=CC=CC=2)[N:3]=1.NCCCN1CC[O:30]CC1>CC(O)C.CO>[NH2:16][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:2](=[O:30])[NH:3]2

Participants

5

Reactant 2

HCID 61055N-(3-Aminopropyl)morpholineHCID 58168281HCID 58168281, compound

Product 1

HCID 68650098HCID 68650098, compoundYield 29.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

(6-Chloro-benzo[c][1,8]naphthyridin-1-yl)-phenyl-amine (25 mg, 0.08 mmol) and N-(3-aminopropyl)morpholine (18 mg, 0.12 mmol) were dissolved in iPrOH (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, filtered through a membrane, and purified via prep-LC-MS. The purified product was converted to the HCl salt via dissolving in methanolic HCl, and concentration on the Genevac to provide 141 (5 mg, 12% yield) as a dark solid. LC-MS (M+H=414, obsd.=414). 1H NMR (400 MHz, d6-DMSO): δ 10.32 (s, 1H), 9.31 (t, 1H), 8.87 (d, 1H), 8.58 (d, 1H), 8.09 (t, 1H), 7.89 (t, 1H), 7.80 (t, 1H), 7.49 (m, 2H), 7.40 (d, 2H), 7.32 (t, 1H), 6.90 (d, 1H), 3.95 (d, 2H), 3.86 (d, 2H), 3.75 (m, 2H), 3.46 (m, 2H), 3.28 (m, 2H), 3.08 (m, 2H), 2.22 (m, 2H).

Workup

  1. filtrationfiltered through a membrane
  2. custompurified via prep-LC-MS
  3. dissolutionvia dissolving in methanolic HCl
  4. concentrationconcentration on the Genevac

Sources & evidence

ORD record
ord-76b6466552b8490787e07bb0a7187da5
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

Loading…