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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one

HRID 2278627
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Reaktionsgleichung

Reaktionsgleichung von HRID 2278627
[N:1]1([C:7]2[N:12]=[C:11]([CH2:13][C:14](=[O:33])[N:15]3[C:23]4[C:18](=[C:19](C5CCCN(CCC)C5)[CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[NH:10][C:9](=[O:34])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.CN(C)[CH2:38][CH2:39][CH2:40]N=C=NCC.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+]>CN(C)C=O.N1C=CC=CC=1>[N:1]1([C:7]2[N:12]=[C:11]([CH2:13][C:14](=[O:33])[N:15]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH:17]4[CH2:38][CH2:39][CH2:40][CH:16]34)[NH:10][C:9](=[O:34])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1
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Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 1360696076-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

Produkt 1

HCID 1360696136-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one
Ausbeute 143,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

320 mg of 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole [reference example 7d] and 424 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are added to a solution of 525 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (obtained in step 2d of example 1d) in 4 ml of N,N-dimethylformamide and 4 ml of pyridine. The reaction mixture is stirred at ambient temperature for 72 hours and then concentrated under reduced pressure. The residue is taken up in a mixture of water and ethyl acetate and the organic phase is washed successively with water, a 1M hydrochloric acid solution and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is triturated from methanol, filtered and washed with diisopropyl ether, so as to give 375 mg of 6-(morpholin-4-yl)-2-[2-oxo-2-(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)ethyl]pyrimidin-4(3H)-one, the characteristics of which are the following:

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is taken up in a mixture of water and ethyl acetate
  3. washthe organic phase is washed successively with water
  4. dry with materiala 1M hydrochloric acid solution and water, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is triturated from methanol
  8. filtrationfiltered
  9. washwashed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2f20f541b9e640b986b009bc55ace125
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133168B2

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