1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Edoxaban

HRID 1361450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361450
[NH2:1][C@@H:2]1[CH2:7][C@@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:5][CH2:4][C@@H:3]1[NH:13][C:14](=[O:25])[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)=[O:16].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:38][N:39]1[CH2:44][CH2:43][C:42]2[N:45]=[C:46]([C:48](O)=[O:49])[S:47][C:41]=2[CH2:40]1.Cl.CN(C)CCCN=C=NCC>CC(N(C)C)=O.O.C(N(CC)CC)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C:14]([NH:13][C@H:3]2[CH2:4][CH2:5][C@H:6]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])[CH2:7][C@H:2]2[NH:1][C:48]([C:46]2[S:47][C:41]3[CH2:40][N:39]([CH3:38])[CH2:44][CH2:43][C:42]=3[N:45]=2)=[O:49])=[O:25])=[N:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 111490315-Methyl-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid--hydrogen chloride (1/1)HCID 59676986EthanediaMide iMpurity F

Produkt 1

HCID 10280735EdoxabanAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

N1-{(1S,2R,4S)-2-Amino-4-[(dimethylamino)carbonyl]cyclohexyl}-N2-(5-chloropyridin-2-yl)ethanediamide (553.4 mg) was dissolved in dimethylacetamide (7 mL), and to the solution were added 1-hydroxybenzotriazole monohydrate (245.1 mg), 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride (386.0 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (345.0 mg) at room temperature. The resultant mixture was stirred for 13 hours, and triethylamine and water were added thereto. The precipitated crystals were collected by filtration, and were dried, to thereby give 674.1 mg of the title compound.

Aufarbeitung

  1. filtrationThe precipitated crystals were collected by filtration
  2. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-797122a54ad7473280dbbe5658c7bec9
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880005B2

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