1,2-Dichloroethane → HCID 66571158, Verbindung

HRID 83614

Reaktionsgleichung

Reaktionsgleichung von HRID 83614
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:48]([NH2:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C=O)C.CCOCC.CCOC(C)=O>[CH2:48]([NH:55][C:20]([CH:17]1[CH2:18][CH2:19][N:14]([C:12]([C:8]2[N:7]([CH2:6][C:5]3[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:11]=[CH:10][CH:9]=2)=[O:13])[CH2:15][CH2:16]1)=[O:22])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 683802051-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid

Produkt 1

HCID 66571158HCID 66571158, VerbindungAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The following was dissolved in anhydrous DMF (3 mL): 1-(1-(4-chlorobenzyl)-1H-pyrrole-2-carbonyl)piperidine-4-carboxylic acid (115 mg, 0.332 mmol), Hunig's Base (0.174 ml, 0.995 mmol), EDC (76 mg, 0.398 mmol), HOBt (60.9 mg, 0.398 mmol), and benzylamine (0.040 ml, 0.365 mmol). This was stirred at room temperature for 1 day with 3 Å molecular sieves. At this time, a 1:1 solution of EtOAc:Et2O (20 mL) was added and the organic layer was washed with 10% aq. Na2CO3 (2×10 mL) and brine (1×10 mL). The organic solution was then dried (anhydrous MgSO4) and concentrated in vacuo. Trituration in Et2O provided 101 mg of the title compound as a fine, ruddy brown solid.

Aufarbeitung

  1. washthe organic layer was washed with 10% aq. Na2CO3 (2×10 mL) and brine (1×10 mL)
  2. dry with materialThe organic solution was then dried (anhydrous MgSO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d09c387e53d24c20a5fb537a9453b272
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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