Diisopropylethylamine → HCID 67187460, Verbindung

HRID 885974

Reaktionsgleichung

Reaktionsgleichung von HRID 885974
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([C:10]3[S:11][C:12]4[C:13](=[O:21])[NH:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]=4[N:18]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.[CH3:49][N:50]1[CH2:55][CH2:54][CH:53]([C:56](O)=[O:57])[CH2:52][CH2:51]1.CCN(C(C)C)C(C)C>CN(C=O)C.O.CC#N>[CH3:19][C:15]1([CH3:20])[NH:14][C:13](=[O:21])[C:12]2[S:11][C:10]([N:6]3[C:5]4[CH:22]=[CH:23][C:2]([NH:1][C:56]([CH:53]5[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]5)=[O:57])=[CH:3][C:4]=4[O:9][CH2:8][CH2:7]3)=[N:18][C:17]=2[CH2:16]1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27600434-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1)HCID 67185695HCID 67185695, Verbindung

Produkt 1

HCID 67187460HCID 67187460, VerbindungAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of Example 233 (0.049 g, 0.15 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.111 g, 0.29 mmol) and 1-methylpiperidine-4-carboxylic acid hydrochloride (0.034 g, 0.19 mmol) in DMF (0.5 mL) was added DIPEA (0.06 mL, 0.35 mmol). The reaction mixture was stirred at r.t. for 16 h. MeCN (1 mL) and water (1 mL) were added. The insoluble material was filtered, and the filtrate concentrated in vacuo. Purification by preparative HPLC (Method 6) gave the title compound (0.035 g, 51%) as a yellow solid. δH (CD3OD) 7.91 (1H, d, J 9.0 Hz), 7.37 (1H, d, J 2.3 Hz), 7.11 (1H, dd, J 8.9 and 2.3 Hz), 4.40-4.30 (2H, m), 4.20-4.09 (2H, m), 3.62 (2H, d, J 12.6 Hz), 3.17-3.02 (2H, m), 2.92 (3H, s), 2.89 (2H, s), 2.76-2.60 (1H, m), 2.34-1.91 (4H, m), 1.39 (6H, s). Exchangeable protons were not observed. LCMS (ES+) 456.21 (M+H)+, RT 1.80 minutes (Method 1).

Aufarbeitung

  1. filtrationThe insoluble material was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by preparative HPLC (Method 6)

Quellen und Nachweise

ORD-Eintrag
ord-fcbfc1827857424ba3909b4ecdeac4af
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242116B2

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