Triethylamine → N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide

HRID 643009

Reaktionsgleichung

Reaktionsgleichung von HRID 643009
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH2:57])[N:53]=[CH:52]2)=[N:49][CH:50]=1>CN(C=O)C.CCOC(C)=O.O>[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH:57][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[N:53]=[CH:52]2)=[N:49][CH:50]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68502878(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine

Produkt 1

HCID 68507465N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamideAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-2-thiophenecarboxylic acid (195 mg, 1.20 mmol) and triethylamine (0.400 mL, 2.87 mmol) in DMF (5 mL), BOP (550 mg, 1.24 mmol) was added. After 5 min of stirring, a solution of (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine (253 mg, 1.00 mmol) in DMF (5 mL) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was purified by HPLC to give N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (85 mg).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-028b648dce5443338baad7827c4126f5
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696352B2

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