Pyrazole → (r)-4-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid (azepan-3-yl)-amide

HRID 2114311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114311
N1C=C[CH:3]=N1.CN([C@@H](C1C=CC=CC=1)C)C([C:10]1[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[NH:12][N:11]=1)=O.ClC1C=CC=CC=1C(Cl)=O.C(OC([N:54]1[CH2:60][CH2:59][CH2:58][CH2:57][C@@H:56]([NH:61][C:62]([O:64]C(C)(C)C)=O)[CH2:55]1)=O)C1C=CC=CC=1.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)CCCCN.N1(N)CCCCC1>>[NH:54]1[CH2:60][CH2:59][CH2:58][CH2:57][C@@H:56]([NH:61][C:62]([C:10]2[C:14]([Br:15])=[C:13]([NH:16][C:17](=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:12]([CH3:3])[N:11]=2)=[O:64])[CH2:55]1

Komponenten

7

Edukt 6

HCID 1048PyrazoleHCID 166581-AminopiperidineHCID 691102-Chlorobenzoyl chlorideHCID 7018770Boc-D-Lys-OHHCID 69152935Benzyl (R)-3-((tert-butoxycarbonyl)amino)azepane-1-carboxylateHCID 178461679HCID 178461679, Verbindung

Produkt 1

HCID 59773409(r)-4-Bromo-5-(2-chloro-benzoylamino)-1-methyl-pyrazole-3-carboxylic acid (azepan-3-yl)-amide

Versuchsvorschrift

The pyrazole acid, prepared by coupling methyl ester 85 (Procedure 26) with 2-chlorobenzoyl chloride (21) followed by hydrolysis and bromination as shown in Procedure 8, was coupled to (R)-3-tert-butoxycarbonylaminoazepane-1-carboxylic acid benzyl ester (prepared as described in Procedure 23 using Boc-D-Lys-OH (Bachem, A-2705) followed by Cbz protection of the piperidine amine using the method of Procedure 30) using Procedure 3. Removal of the Cbz group using the method of Procedure 20 afforded the title compound.

Aufarbeitung

  1. customfollowed by hydrolysis and bromination
  2. customprepared
  3. customRemoval of the Cbz group

Quellen und Nachweise

ORD-Eintrag
ord-068b87414bc64e778bb2510284b30118
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07432379B2

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