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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

HRID 1811665
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1811665
Cl.[Br:2][C:3]1[S:7][C:6]2=[N:8][C:9]([NH2:11])=[CH:10][N:5]2[CH:4]=1.[C:12]([O:16][C:17]([NH:19][C@H:20]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28](O)=[O:29])=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[C:12]([O:16][C:17](=[O:18])[NH:19][C@@H:20]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@@H:24]1[C:28](=[O:29])[NH:11][C:9]1[N:8]=[C:6]2[N:5]([CH:10]=1)[CH:4]=[C:3]([Br:2])[S:7]2)=[O:22])([CH3:15])([CH3:13])[CH3:14]
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Komponenten

5

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10089106(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acidHCID 672405282-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochloride

Produkt 1

HCID 86654641(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester
Ausbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of compound 11 (0.137 mmol), compound 3a (0.206 mmol), and HATU (0.206 mmol) in dimethylformamide (1.5 mL) was added TEA (0.55 mmol) dropwise. The reaction mixture was stirred at 40° C. for 4 hrs. The solvent was removed under reduced pressure and the residue dissolved in a mixture of dichloromethane/methanol (9/1). This mixture was passed through a SCX-2 column and the column was washed three times with the same eluent. The filtrate was concentrated and the residue was purified by chromatography on a silica gel column to give compound 12a as a yellow orange solid in 18% yield. MS (ESI, EI+) m/z=548.24-550.20 (MH+).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in a mixture of dichloromethane/methanol (9/1)
  3. washthe column was washed three times with the same eluent
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-5c8ec60bddf34e5ca00606c59726545d
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08362068B2

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