Diisopropylethylamine → HCID 67005528, Verbindung

HRID 563146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 563146
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=1.ClC(N(C)C)=C(C)C.CCN(C(C)C)C(C)C.[CH2:33]([N:40]1[CH2:45][CH2:44][N:43]([C:46](=[O:68])[C@@H:47]([NH:55][CH2:56][C:57]2[CH:62]=[CH:61][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:59][CH:58]=2)[CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:48]([C@H:47]([N:55]([CH2:56][C:57]1[CH:58]=[CH:59][C:60]([O:63][CH2:64][CH2:65][CH2:66][CH3:67])=[CH:61][CH:62]=1)[C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=1)[C:46]([N:43]1[CH2:42][CH2:41][N:40]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:45][CH2:44]1)=[O:68])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 6880704-(Trifluoromethyl)cinnamic acidHCID 59808329HCID 59808329, Verbindung

Produkt 1

HCID 67005528HCID 67005528, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In an inert atmosphere, trans-4-(trifluoromethyl)cinnamic acid (28 mg, 0.13 mmol) was dissolved in DCM (0.5 mL) followed by the addition of 1-chloro-N,N,2-trimethylpropenylamine (19.4 mg, 0.145 mmol). The mixture was stirred at rt for 30 min followed by the addition of DIPEA (34 mg, 0.26 mmol) and 1-(4-benzyl-piperazin-1-yl)-2-(4-butoxy-benzylamino)-(S)-3-phenyl-propan-1-one (63 mg, 0.13 mmol). Stirring was continued for 30 min. The mixture was concentrated in vacuo and the residue was directly purified by prep. HPLC to give 51 mg (57%) of N—[(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-butoxy-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=1.02 min; [M+H]+=684.49.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 30 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was directly purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-5e836015fad04c1d880496785d57886d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067419B2

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