Diisopropylethylamine → HCID 44464593, Verbindung

HRID 1881701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881701
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[S:42]([N:45]([CH2:49][CH2:50][O:51][CH2:52][C:53](O)=[O:54])[CH:46]1[CH2:48][CH2:47]1)(=[O:44])=[O:43].[F:56][C:57]1[CH:58]=[C:59]([C:63]2([O:69][CH2:70][CH2:71][N:72]3[CH2:76][CH2:75][CH2:74][CH2:73]3)[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[CH:60]=[CH:61][CH:62]=1>O1CCCC1>[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[S:42]([N:45]([CH:46]1[CH2:48][CH2:47]1)[CH2:49][CH2:50][O:51][CH2:52][C:53]([N:66]1[CH2:65][CH2:64][C:63]([C:59]2[CH:60]=[CH:61][CH:62]=[C:57]([F:56])[CH:58]=2)([O:69][CH2:70][CH2:71][N:72]2[CH2:76][CH2:75][CH2:74][CH2:73]2)[CH2:68][CH2:67]1)=[O:54])(=[O:44])=[O:43]

Komponenten

6

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57916232HCID 57916232, VerbindungHCID 57916235HCID 57916235, Verbindung

Produkt 1

HCID 44464593HCID 44464593, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

DIPEA (2 eq.) and HATU (1.2 eq.) were added to a solution of tetrahydrofuran and 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetic acid [acid K] (1 eq.) at 0° C. 4-(3-Fluorophenyl)-4-(2-(pyrrolidin-1-yl)ethoxy)piperidine [amine C] (1.2 eq.) was taken up in tetrahydrofuran (2 ml/mmol) and the solution was rendered basic with DIPEA (2 eq.) and added to the reaction mixture at 0° C. The reaction mixture was stirred at 25° C. for 16 h. The mixture was concentrated to dryness on a rotary evaporator, the residue was taken up in methylene chloride and the mixture was washed with water and sat. sodium chloride solution and dried over sodium sulfate. The organic phase was concentrated and the crude product was purified by means of column chromatography (5% methanol in methylene chloride). Yield: 60%. MS, Rt=3.6 min, m/z=622.4 [MH]+

Aufarbeitung

  1. additionadded to the reaction mixture at 0° C
  2. concentrationThe mixture was concentrated to dryness on a rotary evaporator
  3. washthe mixture was washed with water and sat. sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic phase was concentrated
  6. customthe crude product was purified by means of column chromatography (5% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-1ec14f126924450088744dc979215677
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318769B2

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