Water → HCID 19867682, compound

HRID 1199063Notes

Reaction equation

HRID 1199063 reaction equation
C(N(CC)CC)C.[CH3:8][CH:9]([CH3:14])[CH2:10][CH2:11][CH2:12][NH2:13].Cl[CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[N:17]1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[N:29][C:30]([Cl:36])=[CH:31][CH:32]=2)[N:27]=1.O>CN(C)C=O>[Cl:36][C:30]1[N:29]=[C:28]2[C:33]([CH:34]=[CH:35][C:26]([N:17]3[CH:16]([NH:13][CH2:12][CH2:11][CH2:10][CH:9]([CH3:14])[CH3:8])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:25])=[N:27]2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 219608IsohexylamineHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 19867682HCID 19867682, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Triethylamine (2 cc) and 4-methylpentylamine (2 g) are added to a suspension, maintained under an argon atmosphere, of 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (5 g) in anhydrous dimethylformamide (50 cc). The reaction mixture is stirred for 1 hour 30 minutes at a temperature in the region of 20° C. and then heated with stirring to a temperature of 60° C. for 3 hours. After being cooled, the mixture is poured into ice (100 g) and water (300 cc) and then extracted with dichloromethane (2×200 cc). The organic phases are combined, washed with water (4×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. Ethyl acetate (300 cc) is added to the residue obtained. An insoluble product is removed by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is crystallized successively in ethyl acetate and acetonitrile. 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-methylpentylamino)-1 -isoindolinone (1.4 g), m.p. 131° C., is thereby obtained.

Workup

  1. temperatureheated
  2. stirringwith stirring to a temperature of 60° C. for 3 hours
  3. temperatureAfter being cooled
  4. extractionextracted with dichloromethane (2×200 cc)
  5. washwashed with water (4×50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  9. additionEthyl acetate (300 cc) is added to the residue
  10. customobtained
  11. customAn insoluble product is removed by filtration
  12. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  13. customThe residue obtained
  14. customis crystallized successively in ethyl acetate

Sources & evidence

ORD record
ord-80d0c22a192c402c80f6cdeb4f2f5d45
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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