1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44218283, Verbindung

HRID 46006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46006
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20](O)=[O:21])[CH:13]1[CH2:15][CH2:14]1)(=[O:11])=[O:10].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH:55]1([N:58]2[CH2:63][CH2:62][N:61]([C:64]3([CH2:70][NH:71][C:72](=[O:79])[C:73]4[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=4)[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]3)[CH2:60][CH2:59]2)[CH2:57][CH2:56]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20]([N:67]1[CH2:66][CH2:65][C:64]([CH2:70][NH:71][C:72](=[O:79])[C:73]2[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=2)([N:61]2[CH2:60][CH2:59][N:58]([CH:55]3[CH2:56][CH2:57]3)[CH2:63][CH2:62]2)[CH2:69][CH2:68]1)=[O:21])[CH:13]1[CH2:14][CH2:15]1)(=[O:10])=[O:11]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57453429HCID 57453429, VerbindungHCID 57916235HCID 57916235, Verbindung

Produkt 1

HCID 44218283HCID 44218283, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)-ethoxy)acetic acid AC8 (0.225 mmol) in dichloromethane (10 ml/mmol) was added diisopropyl ethylamine (4 equiv.) at 0° C. followed by the addition of HOBT (1.0 equiv.) and EDCI (1.5 equiv.). The resulting solution was stirred at 25° C. for 15 min. It was again cooled to 0° C. and a solution of N-((4-(4-cyclopropyl-piperazin-1-yl)piperidin-4-yl)methyl)isonicotinamide dihydrochloride AM12 (1.2 equiv.) in DMF (2 ml) was added. The reaction mixture was stirred for 16 h at 25° C. The mixture was diluted with dichloromethane, washed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give the crude product which was purified by column chromatography. Yield: 55%. MS, Rt=2.8 min, m/z=673.4 [MH]+.

Aufarbeitung

  1. temperatureIt was again cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 16 h at 25° C
  3. washwashed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13b1eab9be1543a69f52f40536d97ad1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541573B2

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