1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86609334, Verbindung

HRID 459046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459046
[CH3:1][O:2][C:3]([N:5]([CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:4].[F:14][C:15]1[CH:16]=[C:17]([N:34]2[CH2:38][C@H:37]([CH2:39][N:40]3[CH:44]=[CH:43][N:42]=[N:41]3)[O:36][C:35]2=[O:45])[CH:18]=[CH:19][C:20]=1[C:21]1[CH:22]=[N:23][C:24]([C:27]2[CH2:31][C@@H:30]([CH2:32]O)[O:29][N:28]=2)=[CH:25][CH:26]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([N:5]([CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:32][C@H:30]1[O:29][N:28]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([C:20]3[CH:19]=[CH:18][C:17]([N:34]4[CH2:38][C@H:37]([CH2:39][N:40]5[CH:44]=[CH:43][N:42]=[N:41]5)[O:36][C:35]4=[O:45])=[CH:16][C:15]=3[F:14])=[CH:22][N:23]=2)[CH2:31]1)=[O:11])=[O:4]

Komponenten

7

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneHCID 184429735-[(Methoxycarbonyl)(methyl)amino]pentanoic acid

Produkt 1

HCID 86609334HCID 86609334, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The carbamate prepared as above (0.175 g, 0.93 mmol), (5R)-3-(3-fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1: 0.25 g, 0.57 mmol), 4-dimethylaminopyridine (0.01 g, 0.08 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.19 g, 0.99 mmol) were combined in DMF (2 ml). The suspension was allowed to stir for 3.5 hours at room temperature resulting in a clear solution. The mixture was then diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. The residue obtained upon filtration and evaporation was purified via chromatography (silica gel, 0.5 to 10% methanol in dichloromethane). Evaporation of the product containing fractions and trituration of the resulting solid with diethyl ether yielded the title compound as a white powder (0.18 g), melting point: 82° C.

Aufarbeitung

  1. customresulting in a clear solution
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe residue obtained upon filtration and evaporation
  5. customwas purified via chromatography (silica gel, 0.5 to 10% methanol in dichloromethane)
  6. customEvaporation of the product
  7. additioncontaining fractions and trituration of the resulting solid with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f88fbe6980b34949a78027d335b08d6a
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192974B2

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