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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 11613717, Verbindung

HRID 1713999
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1713999
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][O:14][C:15](=[O:21])[CH2:16][S:17]([NH2:20])(=[O:19])=[O:18].[CH:22]1([C:28]2[C:29]3[CH:30]=[CH:31][C:32]([C:50](O)=[O:51])=[CH:33][C:34]=3[N:35]3[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][C:38]4[CH:44]=[C:45]([O:48][CH3:49])[CH:46]=[CH:47][C:37]=4[C:36]=23)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][O:14][C:15](=[O:21])[CH2:16][S:17]([NH:20][C:50]([C:32]1[CH:31]=[CH:30][C:29]2[C:28]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:36]3[C:37]4[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:38]=4[CH2:39][N:40]([CH3:43])[CH2:41][CH2:42][N:35]3[C:34]=2[CH:33]=1)=[O:51])(=[O:19])=[O:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21287077Methyl 2-sulfamoylacetateHCID 42640442HCID 42640442, Verbindung

Produkt 1

HCID 11613717HCID 11613717, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.6 eq of 1-ethyl-(3-dimethylaminopropyl)carbodiimide HCl salt was added to a mixture of 2.7 eq of DMAP, 1.6 eq of methyl(aminosulfonyl)acetate and the hydrochloride salt of 14-cyclohexyl-3-methoxy-6-methyl-5,6,7,8-tetrahydroindolo[2,1-a][2,5]-benzodiazocine-11-carboxylic acid (from Example 4) in DCM (0.02 M). The reaction was stirred at RT overnight before being partitioned between aqueous HCl (1 N) and EtOAc. The organics were washed with saturated aqueous NaHCO3, water and brine before being dried over Na2SO4, filtered and concentrated in vacuo. The crude was then purified by RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 30×50 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder (18%).

Aufarbeitung

  1. custombefore being partitioned between aqueous HCl (1 N) and EtOAc
  2. washThe organics were washed with saturated aqueous NaHCO3, water and brine
  3. dry with materialbefore being dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was then purified by RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 30×50 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA)
  7. additionFractions containing the pure compound
  8. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-3ff17dbf438849369a2d81b324d52baa
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795247B2

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