1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-((1-(2-(2-(N-Cyclopropyl-2-(trifluoromethyl)phenyl-sulfonamido)ethoxy)acetyl)-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)-methyl)isonicotinamide

HRID 46010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46010
[CH:1]1([N:4]([CH2:18][CH2:19][O:20][CH2:21][C:22](O)=[O:23])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH:57]1([N:60]2[CH2:65][CH2:64][N:63]([C:66]3([CH2:72][NH:73][C:74](=[O:81])[C:75]4[CH:80]=[CH:79][N:78]=[CH:77][CH:76]=4)[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]3)[CH2:62][CH2:61]2)[CH2:59][CH2:58]1>ClCCl.CN(C=O)C>[CH:1]1([N:4]([CH2:18][CH2:19][O:20][CH2:21][C:22]([N:69]2[CH2:68][CH2:67][C:66]([CH2:72][NH:73][C:74](=[O:81])[C:75]3[CH:80]=[CH:79][N:78]=[CH:77][CH:76]=3)([N:63]3[CH2:62][CH2:61][N:60]([CH:57]4[CH2:58][CH2:59]4)[CH2:65][CH2:64]3)[CH2:71][CH2:70]2)=[O:23])[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:15])([F:17])[F:16])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57453429HCID 57453429, VerbindungHCID 57989586HCID 57989586, Verbindung

Produkt 1

HCID 44218120N-((1-(2-(2-(N-Cyclopropyl-2-(trifluoromethyl)phenyl-sulfonamido)ethoxy)acetyl)-4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)-methyl)isonicotinamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(2-(N-cyclopropyl-2-(trifluoromethyl)phenylsulfonamido)-ethoxy)acetic acid AC9 (0.472 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 resultant solution was stirred at 25° C. for 15 min. It was again cooled to 0° C. and a solution of N-((4-(4-cyclopropylpiperazin-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=693.5 [MH]+.

Aufarbeitung

  1. washwashed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-376c4504e34c4fa09e26ee5b16e13d8d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541573B2

Notizen zur Reaktion

Wird geladen…