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

HRID 418517
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 418517
[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:19])[C:14]=2[NH2:18])[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2].[F:21][C:22]1[CH:23]=[C:24]([CH2:32][C:33](O)=[O:34])[CH:25]=[CH:26][C:27]=1[C:28]([F:31])([F:30])[F:29].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CN(C)C=O>>[C:1]([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:19])[C:14]=2[NH:18][C:33](=[O:34])[CH2:32][C:24]2[CH:25]=[CH:26][C:27]([C:28]([F:29])([F:30])[F:31])=[C:22]([F:21])[CH:23]=2)[C:9]1=[O:20])[CH3:7])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27375913-Fluoro-4-(trifluoromethyl)phenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59515683(R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Produkt 1

HCID 59515877(R)-2-(5-(2-(3-Fluoro-4-(trifluoromethyl)phenyl)acetamido)-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A round bottom flask was charged with (R)-2-(5-amino-6-methyl-1-oxoisoquinolin-2(1H)-yl)propyl acetate (175 mg, 0.000638 mol), 2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (210 mg, 0.00096 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (610 mg, 0.0016 mol), N,N-diisopropylethylamine (0.28 mL, 0.0016 mol) and N,N-dimethylformamide (8 mL, 0.1 mol). The reaction mixture was stirred at 45° C. for 24 hours. The reaction was quenched with water and extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried. The solvent was removed under reduced pressure and the residue was purified by flash chromatography to afford the product as a light yellow oil.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-69459c7411a34bea8667d5c3143ac58a
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093265B2

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