1,3-Propanediamine → HCID 44280404, compound

HRID 646598Notes

Reaction equation

HRID 646598 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:20]([F:23])([F:22])[F:21])=[N:7]2.[NH2:24][CH2:25][CH2:26][CH2:27][NH2:28]>C1(C)C=CC=CC=1>[NH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:20]([F:23])([F:22])[F:21])=[N:7]2

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 59215154HCID 59215154, compound

Product 1

HCID 44280404HCID 44280404, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-7-(4-methoxy-phenyl)-2-trifluoromethyl-[1,6]naphthyridine (55 mg, 0.2 mmol) and 1,3-diaminopropane (2.5 mL) in a sealed reaction vessel was heated at 100° C. for 3 hours. The mixture was diluted with toluene and concentrated three times to azeotropically remove excess 1,3-diaminopropane. The residue was diluted with EtOAc, washed sequentially with sat. NaHCO3, H2O, sat. NaCl, dried over Na2SO4, and concentrated giving the title compound (60 mg, quantitative) as a yellow solid.

Workup

  1. customin a sealed reaction vessel
  2. concentrationconcentrated three times to azeotropically remove excess 1,3-diaminopropane
  3. additionThe residue was diluted with EtOAc
  4. washwashed sequentially with sat. NaHCO3, H2O, sat. NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fd351de10c641abbc24fe488b58dcf4
Source dataset
uspto-grants-2010_04
Patent number
US07705151B2

Reaction notes

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