Cyclopentylamine → HCID 18956298, compound

HRID 2379890Notes

Reaction equation

HRID 2379890 reaction equation
[NH2:1][C:2](=[N:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([C:16]([O:18]C)=O)[CH:15]=2)[N:9]=1)[NH2:3].[CH:20]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21]1.C[O-].[Na+]>CO>[CH:20]1([NH:25][C:16]([C:14]2[CH:15]=[C:10]([C:8]3[N:9]=[C:5]([N:4]=[C:2]([NH2:1])[NH2:3])[S:6][CH:7]=3)[CH:11]=[N:12][CH:13]=2)=[O:18])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 104687342-(Diaminomethyleneamino)-4-(5-methoxycarbonylpyridin-3-yl)thiazoleHCID 10942334Sodium Methoxide

Product 1

HCID 18956298HCID 18956298, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-(diaminomethyleneamino)-4-(5-methoxycarbonylpyridin-3-yl)thiazole (2.0 g), cyclopentylamine (3.7 g) and 28% sodium methoxide methanolic solution (5 ml) in methanol (50 ml) was refluxed for 2 hours. The solvent was removed under reduced pressure. The residue was dissolved in water (50 ml). The mixture was extracted with a mixture of ethyl acetate (150 ml) and tetrahydrofuran (50 ml). The extract was dried over magnesium sulfate and then was evaporated. Recrystallization from a mixture of methanol and diisopropyl ether afforded 4-(5-cyclopentylaminocarbonylpyridin-3-yl)-2-(diaminomethyleneamino)thiazole (0.2 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (50 ml)
  4. extractionThe mixture was extracted with a mixture of ethyl acetate (150 ml) and tetrahydrofuran (50 ml)
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customwas evaporated
  7. customRecrystallization
  8. additionfrom a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-d4e9c684680345ed818e103b495688f6
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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