Dichloromethane → (R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate

HRID 418537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418537
C(N(CC)CC)C.[F:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([NH:22][C:23]2[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]3[C:24]=2[CH:25]=[CH:26][N:27]([C@H:35]([CH3:38])[CH2:36][OH:37])[C:28]3=[O:34])=[O:21])[CH:12]=[CH:13][C:14]=1[C:15]([F:18])([F:17])[F:16].[CH3:39][S:40](Cl)(=[O:42])=[O:41].C(Cl)Cl>CN(C)C1C=CN=CC=1>[CH3:39][S:40]([O:37][CH2:36][C@H:35]([N:27]1[CH:26]=[CH:25][C:24]2[C:29](=[CH:30][CH:31]=[C:32]([CH3:33])[C:23]=2[NH:22][C:20](=[O:21])[CH2:19][C:11]2[CH:12]=[CH:13][C:14]([C:15]([F:18])([F:16])[F:17])=[C:9]([F:8])[CH:10]=2)[C:28]1=[O:34])[CH3:38])(=[O:42])=[O:41]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 25013922(R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide

Produkt 1

HCID 59845709(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

Triethylamine (0.2 g, 0.002 mol) was added to a solution of (R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-N-(2-(1-hydroxypropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide (0.5 g, 0.001 mol), methanesulfonyl chloride (0.16 g, 0.0014 mol) and 4-dimethylaminopyridine (10 mg, 0.0001 mol) in methylene chloride (10 mL, 0.2 mol). The mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the mixture was purified via flash chromatography to afford the desired product as a white solid.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. customthe mixture was purified via flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ff868edc6e84617af4f0b72a5834cb4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093265B2

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