Diisopropylethylamine → HCID 66819997, Verbindung

HRID 241025

Reaktionsgleichung

Reaktionsgleichung von HRID 241025
[CH2:1]([O:8][C:9]([N:11]([CH3:16])[CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[Br:50][C:51]1[CH:52]=[C:53]([NH2:58])[C:54]([NH2:57])=[N:55][CH:56]=1>CN(C)C=O.C(OCC)(=O)C>[C:2]1([CH2:1][O:8][C:9](=[O:10])[N:11]([CH2:12][C:13]([NH:58][C:53]2[C:54]([NH2:57])=[N:55][CH:56]=[C:51]([Br:50])[CH:52]=2)=[O:15])[CH3:16])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 97053N-CarbobenzoxysarcosineHCID 6911565-Bromopyridine-2,3-diamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 66819997HCID 66819997, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-[(benzyloxycarbonyl)(methyl)amino]acetic acid (0.42 g, 1.88 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.75 g, 1.97 mmol) in N,N-dimethylformamide (3.0 mL), N,N-diisopropylethylamine (0.72 mL, 4.12 mmol) was added and the reaction mixture was stirred for 30 minutes at room temperature, followed by the addition of 5-bromo-2,3-diaminopyridine (0.35 g, 1.86 mmol), then stirred for 16 hours. It was diluted with ethyl acetate (50 mL), washed with aqueous lithium chloride (2×20 mL) and brine, dried over sodium sulfate, filtered and concentrated. Gradient flash chromatography (35% to 85% ethyl acetate in hexane) provided phenylmethyl{2-[(2-amino-5-bromopyridin-3-yl)amino]-2-oxoethyl}methylcarbamate (0.70 g, 96%). MS (EI) for C16H17BrN4O3: 394 (MH+).

Aufarbeitung

  1. additionwas added
  2. stirringstirred for 16 hours
  3. washwashed with aqueous lithium chloride (2×20 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17e39c65e19e4534a58b648a83dd7b74
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

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