1,2-Dichloroethane → N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}-1H-pyrrole-2-carboxamide

HRID 908258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908258
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][CH2:8][C:9]1[N:10]=[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]2[CH:21]=1.[F:22][C:23]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[C:24]=1[C:25]([C:27]1[CH:28]=[C:29]([C:32](O)=[O:33])[NH:30][CH:31]=1)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CCOC(C)=O.CN(C=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][N:7]([CH2:8][C:9]1[N:10]=[C:11]2[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[CH:13][N:12]2[CH:21]=1)[C:32]([C:29]1[NH:30][CH:31]=[C:27]([C:25](=[O:26])[C:24]2[C:23]([F:22])=[CH:38][C:37]([F:39])=[CH:36][C:35]=2[F:40])[CH:28]=1)=[O:33]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acidHCID 580248001-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine

Produkt 1

HCID 58024797N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}-1H-pyrrole-2-carboxamideAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a DMF 10 mL solution of 1-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine (1.13 g, 3.75 mmol) were added 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid (1.06 g, 3.94 mmol), EDC (1.08 g, 5.63 mmol), HOBt (862 mg, 5.63 mmol) and triethyl amine (1.57 mL, 11.25 mmol). The mixture was stirred at room temperature overnight. The resulting suspension was diluted with EtOAc. The organic phase was washed with sat. ammonium chloride aq., sat. aq. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered, concentrated and chromatographed on silica gel eluting with a gradient solvent mixture (100% DCM to 5% MeOH-DCM) to give the title compound as foam (744 mg). LC/MS: m/z 533(M+H).

Aufarbeitung

  1. washThe organic phase was washed with sat. ammonium chloride aq., sat. aq. sodium bicarbonate aq. and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with a gradient solvent mixture (100% DCM to 5% MeOH-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-fe4f68fc376e402fbefd3cd6d910a3d3
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017605B2

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