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Dimethylformamide → (S)-2-(5-(2-(3,4-Dichlorophenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide

HRID 1161198
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1161198
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].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.[NH2:51][C:52]1[CH:61]=[CH:60][CH:59]=[C:58]2[C:53]=1[CH:54]=[CH:55][N:56]([C@@H:63]([CH3:67])[C:64]([NH2:66])=[O:65])[C:57]2=[O:62]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:51][C:52]2[CH:61]=[CH:60][CH:59]=[C:58]3[C:53]=2[CH:54]=[CH:55][N:56]([C@@H:63]([CH3:67])[C:64]([NH2:66])=[O:65])[C:57]3=[O:62])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]
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Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 798743,4-Dichlorophenylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59515789(S)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propanamide

Produkt 1

HCID 59515801
(S)-2-(5-(2-(3,4-Dichlorophenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propanamide

Versuchsvorschrift

To a stirred solution of 3,4-dichlorophenyl acetic acid (0.12 g, 0.00056 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.3 g, 0.0009 mol) and N,N-diisopropylethylamine (0.2 mL, 0.0009 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) was added (S)-2-(5-amino-1-oxoisoquinolin-2(1H)-yl)propanamide (0.10 g, 0.00043 mol). The reaction was stirred for 16 h at room temperature. The reaction was quenched with water, extracted with dichloromethane, washed with 2N HCl, saturated sodium bicarbonate solution, brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (12 g, 0-10% MeOH/DCM) to yield the product as a white solid.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washwashed with 2N HCl, saturated sodium bicarbonate solution, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography (12 g, 0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-191b786f13184b5dbcc374cc276072ef
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816371B2

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