Diisopropylethylamine → HCID 86296367, Verbindung

HRID 930827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930827
[F:1][C:2]1[O:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:45]=[CH:46][C:47]([Cl:66])=[C:48]([C:50]2[N:51]=[C:52]3[N:57]=[CH:56][C:55]([NH:58][C:59](=[O:64])[O:60][CH:61]([CH3:63])[CH3:62])=[CH:54][N:53]3[CH:65]=2)[CH:49]=1>CN(C=O)C>[Cl:66][C:47]1[CH:46]=[CH:45][C:44]([NH:43][C:7]([C:5]2[O:6][C:2]([F:1])=[CH:3][CH:4]=2)=[O:9])=[CH:49][C:48]=1[C:50]1[N:51]=[C:52]2[N:57]=[CH:56][C:55]([NH:58][C:59](=[O:64])[O:60][CH:61]([CH3:62])[CH3:63])=[CH:54][N:53]2[CH:65]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 213638875-Fluoro-2-furancarboxylic acidHCID 90444845HCID 90444845, Verbindung

Produkt 1

HCID 86296367HCID 86296367, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 40 mL vial isopropyl (2-(5-amino-2-chlorophenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (I-9) (30 mg, 0.09 mmol) was dissolved in DMF (Volume: 0.3 mL). 5-fluorofuran-2-carboxylic acid (11 mg, 0.09 mmol) was then added to the reaction mixture followed by HATU (65.98 mg, 0.17 mmol) and (iPr)2NEt (0.043 mL, 0.26 mmol). The reaction was stirred at rt for 8 hrs. The reaction was monitored was LCMS which indicated the reaction was complete with a new peak of desired mass was observed (M+H=468.1). The reaction mixture was quenched with water and extracted with ethyl acetate (3×5 mL). Combined all organics, dried over sodium sulfate and concentrated under reduce pressure. The crude reaction purified by reverse phase HPLC yeild 2-(2-chloro-5-(5-fluorofuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (1). The TFA salt was neutralized to a free base by a HCO3 column. 1H NMR (400 MHz, DMSO) δ 10.41 (s, 1H), 10.01 (s, 1H), 9.31 (s, 1H), 8.69 (s, 1H), 8.61 (d, J=2.7, 1H), 8.51 (d, J=2.7, 1H), 7.87 (dd, J=2.7, 8.8, 1H), 7.53 (d, J=8.7, 1H), 7.47 (t, J=3.6, 1H), 6.11 (dd, J=3.7, 7.1, 1H), 5.03-4.85 (m, 1H), 1.29 (d, J=6.2, 6H). M/Z=(458.1M+1). RT=1.64 min.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude reaction
  6. custompurified by reverse phase HPLC yeild 2-(2-chloro-5-(5-fluorofuran-2-carboxamido)phenyl)imidazo[1,2-a]pyrimidin-6-yl)carbamate (1)

Quellen und Nachweise

ORD-Eintrag
ord-692ffe6ee91d44f48e5bfb31dc6331b7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296754B2

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