Isobutyl chloroformate → N-((S)-1-((S)-1-amino-4-methyl-1-oxopentan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide

HRID 242476

Reaktionsgleichung

Reaktionsgleichung von HRID 242476
[CH3:1][C:2]([CH3:30])([CH3:29])[C@H:3]([NH:7][C:8]([N:10]1[C:18]2[CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][C:13]=2[C:12]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:11]1)=[O:9])[C:4]([OH:6])=O.CCN(C(C)C)C(C)C.C(OC(Cl)=O)C(C)C.[NH2:48][C@H:49]([C:54]([NH2:56])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52]>C(Cl)Cl>[NH2:56][C:54](=[O:55])[C@@H:49]([NH:48][C:4](=[O:6])[C@@H:3]([NH:7][C:8]([N:10]1[C:18]2[CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][C:13]=2[C:12]([C:20]2[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=2[F:28])=[N:11]1)=[O:9])[C:2]([CH3:30])([CH3:1])[CH3:29])[CH2:50][CH:51]([CH3:53])[CH3:52]

Komponenten

6

Edukt 4

HCID 62365Isobutyl chloroformateHCID 69640LeucinamideHCID 81531Diisopropylethylamine2×HCID 46861922(S)-3,3-dimethyl-2-(5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamido)butanoic acid

Produkt 1

HCID 46861923N-((S)-1-((S)-1-amino-4-methyl-1-oxopentan-2-ylamino)-3,3-dimethyl-1-oxobutan-2-yl)-5-methyl-3-(2,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 71 (40 mg) in DCM was added DIEA (45 uL) followed by isobutylchloroformate (26 uL). After stirring at room temperature for 30 min, leucine amide (18 mg) and DIEA (25 uL) was added and stirred for 1 h. The reaction mixture was evaporated and dissolved in MeOH, and purified with a preparative LC-MS to give compound 72. LCMS (+ESI) m/z=537.3 [M+H]+.

Aufarbeitung

  1. stirringstirred for 1 h
  2. customThe reaction mixture was evaporated
  3. dissolutiondissolved in MeOH
  4. custompurified with a preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-eda2cff38ef04079b11b8b7e41454a5d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653127B2

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