Diisopropylethylamine → HCID 25206131, Verbindung

HRID 387639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387639
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.[O:30]=[C:31]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([C:41](O)=[O:42])[C:35]=2[CH2:34][CH2:33][N:32]1[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)C.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:41]([C:36]1[C:35]2[CH2:34][CH2:33][N:32]([CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:31](=[O:30])[C:40]=2[CH:39]=[CH:38][CH:37]=1)=[O:42])[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

9

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68469137HCID 68469137, VerbindungHCID 86643873HCID 86643873, VerbindungHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 25206131HCID 25206131, VerbindungAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

326 mg of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)butan-2-ol hydrochloride (2:1), 180 mg of 1-oxo-2-pentyl-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid, 14 mg of hydroxybenzotriazole, 165 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.47 cm3 of N,N-diisopropylethylamine in 18 cm3 of dichloromethane are stirred for 20 h at a temperature close to 20° C. 10 cm3 of water and dichloromethane are added to the reaction medium. The suspension is filtered, washed successively with water and dichloromethane. The solid obtained is taken up in ethyl ether, filtered, washed with ethyl ether and dried under vacuum at 20° C. 360 mg of N-[(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]-1-oxo-2-pentyl-1,2,3,4-tetrahydroisoquinoline-5-carboxamide are obtained in the form of a white solid.

Aufarbeitung

  1. customclose to 20° C
  2. filtrationThe suspension is filtered
  3. washwashed successively with water and dichloromethane
  4. customThe solid obtained
  5. filtrationfiltered
  6. washwashed with ethyl ether
  7. customdried under vacuum at 20° C

Quellen und Nachweise

ORD-Eintrag
ord-5cf512d38e904e35a981dbc59998b077
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372864B2

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