Diisopropylethylamine → tert-butyl-N-[1-[(1-bromoisoquinolin-3-yl)amino]-1-oxopropan-2-yl]carbamate

HRID 535385

Reaktionsgleichung

Reaktionsgleichung von HRID 535385
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[C:28]([NH2:36])[N:27]=1.[CH3:37][C:38]([O:41][C:42]([NH:44][CH:45]([CH3:49])[C:46](O)=[O:47])=[O:43])([CH3:40])[CH3:39].CCN(C(C)C)C(C)C>CC(N(C)C)=O>[C:38]([O:41][C:42](=[O:43])[NH:44][CH:45]([CH3:49])[C:46]([NH:36][C:28]1[N:27]=[C:26]([Br:25])[C:35]2[C:30]([CH:29]=1)=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:47])([CH3:40])([CH3:37])[CH3:39]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2684712-N-Boc-aminopropionic acidHCID 2898451-Bromoisoquinolin-3-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 86694369tert-butyl-N-[1-[(1-bromoisoquinolin-3-yl)amino]-1-oxopropan-2-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

HATU (7.5 g, 19.7 mmol) is added to a mixture of 1-bromoisoquinolin-3-amine (2.0 g, 9.0 mmol), 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (1.7 g, 9.0 mmol) and DIPEA (3.4 ml, 200 mmol) in DMA (10 ml). After stirring for 3 days at RT the mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 3.3 g (94%). HPLC-MS: M−H=392/394; tR=1.97 min (*Method—1).

Aufarbeitung

  1. concentrationis concentrated in vacuo
  2. customthe product purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-107c3cf8150b4ddfbde129b01d1e5dc7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859541B2

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