Dimethylformamide → (R)-2-(5-(2-(4-Chloro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161204
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].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.[NH2:54][C:55]1[CH:64]=[CH:63][CH:62]=[C:61]2[C:56]=1[CH:57]=[CH:58][N:59]([C@H:66]([CH3:70])[C:67]([NH2:69])=[O:68])[C:60]2=[O:65]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:54][C:55]2[CH:64]=[CH:63][CH:62]=[C:61]3[C:56]=2[CH:57]=[CH:58][N:59]([C@H:66]([CH3:70])[C:67]([NH2:69])=[O:68])[C:60]3=[O:65])=[O:11])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13]

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 35198824-Chloro-3-(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 59515719(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide

Produkt 1

HCID 59515771(R)-2-(5-(2-(4-Chloro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide

Versuchsvorschrift

A round bottom flask was charged with 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (0.13 g, 0.00056 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.3 g, 0.0009 mol), N,N-diisopropylethylamine (0.2 mL, 0.0009 mol), N,N-dimethylformamide (3 mL, 0.04 mol) and (R)-2-(5-amino-1-oxoisoquinolin-2(1H)-yl)propanamide (0.1 g, 0.0004 mol). The reaction was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the residue purified by flash chromatography (12 g, 0-10% MeOH/DCM) to get the product as white solid. MS m/z=451.8(M+H). 1H NMR (400 MHz; DMSO-d6) δ 10.10 (s, 1H), 8.07(d, J=8.42 Hz, 1H), 7.89 (s, 1H), 7.82 (d, J=8.47 Hz, 1H) 7.73-7.68 (m, 2H), 7.63 (s, 1H), 7.46 (d, J=7.57 Hz, 2H), 7.23 (bs, 1H), 6.68 (d, J=8.02 Hz, 1H), 5.50-5.45 (q, J=7.24 Hz, 1H), 3.92 (s, 2H), 1.54 (d, J=7.66 Hz, 3H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by flash chromatography (12 g, 0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8153106bc92947aab147924dd9718e44
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816371B2

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