1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[(1R*,2R*)-2-Aminocyclopentyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride

HRID 459466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459466
C(O[C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:14])=[O:7])(C)(C)C.[CH3:15][N:16]1[CH2:21][CH2:20][C:19]2[N:22]=[C:23](C([O-])=O)[S:24][C:18]=2[CH2:17]1.[Li+].[ClH:29].CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[ClH:29].[CH3:15][N:16]1[CH2:21][CH2:20][C:19]2[N:22]=[C:23]([C:6]([NH:8][C@@H:9]3[CH2:13][CH2:12][CH2:11][C@H:10]3[NH2:14])=[O:7])[S:24][C:18]=2[CH2:17]1

Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 17040217rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamateHCID 23704331Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Produkt 1

HCID 18442877N-[(1R*,2R*)-2-Aminocyclopentyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochlorideAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(±)-trans-N-tert-Butoxycarbonyl-1,2-cyclopentane-diamine (175 mg) was dissolved in N,N-dimethylformamide (3 ml), and to the solution lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (purity: 90%, 258 mg), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (252 mg) and 1-hydroxybenzo-triazole monohydrate (60 mg) were added. The mixture was stirred at room temperature for 2 days. The solvent was distilled off under reduced pressure using a pump, and dichloromethane and a saturated solution of sodium hydrogencarbonate were added to the residue to separate an organic layer. The resultant organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by medium-pressure flash column chromatography on silica gel (dichloromethane:methanol=47:3). The resultant pale yellow oil was dissolved in a saturated ethanol solution (5 ml) of hydrochloric acid, and the solution was stirred at room temperature for 1 hour. Ethyl acetate was then added, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue to collect precipitate by filtration, thereby obtaining the title compound (120 mg) as a pale yellow solid.

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona saturated solution of sodium hydrogencarbonate were added to the residue
  3. customto separate an organic layer
  4. washThe resultant organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by medium-pressure flash column chromatography on silica gel (dichloromethane:methanol=47:3)
  8. dissolutionThe resultant pale yellow oil was dissolved in a saturated ethanol solution (5 ml) of hydrochloric acid
  9. stirringthe solution was stirred at room temperature for 1 hour
  10. additionEthyl acetate was then added
  11. distillationthe solvent was distilled off under reduced pressure
  12. additionEthyl acetate was added to the residue
  13. customto collect precipitate
  14. filtrationby filtration

Quellen und Nachweise

ORD-Eintrag
ord-376bffb82049421d82ad990050cd07ec
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192968B2

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