1-(3-Aminopropyl)-4-methylpiperazine → HCID 5327878, compound

HRID 1586418Notes

Reaction equation

HRID 1586418 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=2[CH:10]=1.[NH2:23][CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[O:21])[N:19]([CH3:22])[C:12]2[N:13]=[C:14]([NH:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 107367016-(2,6-Dichlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 5327878HCID 5327878, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 0.152 g (0.43 nmmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 1.0 g (6.40 mmol) of 1-(3-aminopropyl)-4-methylpiperazine was heated with stirring in a 170° C. oil bath (pot T=ca. 160° C.) for 3 hours. The excess amine was evaporated at reduced pressure. Water (5 mL) was added, and the separated gum was extracted into 50 mL of 10% methylene chloride-ether. The organic phase was washed three times with 10 mL of water, dried (potassium carbonate), charcoaled, filtered, and concentrated. The remaining gum was dissolved in 3 mL of ether. The crystals that separated on inducement were filtered and washed with ether; wt 0.033 g; mp 170-172° C.

Workup

  1. temperaturewas heated
  2. customThe excess amine was evaporated at reduced pressure
  3. additionWater (5 mL) was added
  4. extractionthe separated gum was extracted into 50 mL of 10% methylene chloride-ether
  5. washThe organic phase was washed three times with 10 mL of water
  6. dry with materialdried (potassium carbonate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe remaining gum was dissolved in 3 mL of ether
  10. customThe crystals that separated on inducement
  11. filtrationwere filtered
  12. washwashed with ether

Sources & evidence

ORD record
ord-afd6100472754ead88576adaf4a10144
Source dataset
uspto-grants-1999_08
Patent number
US05945422

Reaction notes

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