N,N-Dimethyl-1,3-propanediamine → HCID 19867671, compound

HRID 1199048Notes

Reaction equation

HRID 1199048 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].Cl[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[N:22][C:23]([Cl:29])=[CH:24][CH:25]=2)[N:20]=1>O1CCCC1>[Cl:29][C:23]1[N:22]=[C:21]2[C:26]([CH:27]=[CH:28][C:19]([N:10]3[CH:9]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]3=[O:18])=[N:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 19867671HCID 19867671, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

3-Dimethylaminopropylamine (4.1 g) is added at a temperature in the region of 20° C. to a suspension of 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (6.6 g) in anhydrous tetrahydrofuran (100 cc), and the reaction mixture is heated to reflux for 6 hours. After the reaction mixture has been stirred for a further 20 hours at a temperature in the region of 20° C., it is filtered. The isolated solid is washed with ethyl acetate (3×25 cc). The filtrate is washed with distilled water (3×25 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. 1N aqueous hydrochloric acid solution (20 cc) is added to the residue obtained. An insoluble product is separated by filtration, washed with 1N aqueous hydrochloric acid solution (2×5 cc) and then discarded. The aqueous filtrates are combined and alkalinized with a saturated aqueous potassium bicarbonate solution to a pH in the region of 8, and then extracted with ethyl acetate (3×40 cc). The organic phases are combined, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After recrystallization in ethyl acetate, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(3-dimethylaminopropylamino)-1-isoindolinone (3 g), m.p. 143° C., is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 6 hours
  3. filtrationis filtered
  4. washThe isolated solid is washed with ethyl acetate (3×25 cc)
  5. washThe filtrate is washed with distilled water (3×25 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  9. addition1N aqueous hydrochloric acid solution (20 cc) is added to the residue
  10. customobtained
  11. customAn insoluble product is separated by filtration
  12. washwashed with 1N aqueous hydrochloric acid solution (2×5 cc)
  13. extractionextracted with ethyl acetate (3×40 cc)
  14. dry with materialdried over magnesium sulphate
  15. filtrationfiltered
  16. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  17. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-728d465a42fb4d84bc5759b87e3515a2
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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