Diisopropylethylamine → HCID 25206449, Verbindung

HRID 387654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387654
Cl.[NH2:2][C@@H:3]([CH2:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=1)[C@H:4]([OH:20])[CH2:5][NH:6][C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH2:9][CH2:8]1.[CH3:30][N:31]([S:53]([CH3:56])(=[O:55])=[O:54])[C:32]1[CH:33]=[C:34]([C:50](O)=[O:51])[C:35]2[CH2:36][CH2:37][N:38]([CH:43]([CH2:47][CH2:48][CH3:49])[CH2:44][CH2:45][CH3:46])[C:39](=[O:42])[C:40]=2[CH:41]=1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>ClCCl.O>[F:29][C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([F:28])[CH:25]=1)[CH2:21][C@H:3]([NH:2][C:50]([C:34]1[C:35]2[CH2:36][CH2:37][N:38]([CH:43]([CH2:47][CH2:48][CH3:49])[CH2:44][CH2:45][CH3:46])[C:39](=[O:42])[C:40]=2[CH:41]=[C:32]([N:31]([CH3:30])[S:53]([CH3:56])(=[O:55])=[O:54])[CH:33]=1)=[O:51])[C@H:4]([OH:20])[CH2:5][NH:6][C:7]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH2:9][CH2:8]1

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68469685HCID 68469685, VerbindungHCID 86643873HCID 86643873, VerbindungHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 25206449HCID 25206449, VerbindungAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Poured into a suspension of 233 mg of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride (2:1), 278 mg of 7-[methyl(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid, 12 mg of hydroxybenzotriazole and 142 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 10 cm3 of dichloromethane is 0.4 cm3 of N,N-diisopropylethylamine at a temperature close to 20° C. The solution is kept stirring for 20 h at a temperature close to 20° C. 20 cm3 of water are added to the reaction medium. After decanting, the organic phase is filtered through a pellet of 15 g of 40-63 μm silica. The silica pellet is washed firstly with 150 cm3 of dichloromethane then secondly with 150 cm3 of a mixture of 50% ethyl acetate/50% dichloromethane. This second filtrate is concentrated using a rotary evaporator under reduced pressure (5 kPa). 330 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-7-[methyl(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are obtained in the form of a white foam.

Aufarbeitung

  1. customclose to 20° C
  2. customclose to 20° C
  3. customAfter decanting
  4. filtrationthe organic phase is filtered through a pellet of 15 g of 40-63 μm silica
  5. washThe silica pellet is washed firstly with 150 cm3 of dichloromethane
  6. concentrationThis second filtrate is concentrated
  7. customa rotary evaporator under reduced pressure (5 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-b10b036c503c4169b2b9c62b62b15e2d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372864B2

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