Diisopropylethylamine → HCID 178494101, Verbindung

HRID 470356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470356
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[NH:17][C:18]2[CH:24]=[C:23]([C:25]([OH:27])=O)[CH:22]=[CH:21][C:19]=2[N:20]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)[CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]2[CH:43]=[CH:44][C:45]([NH:48][C:25]([C:23]3[CH:22]=[CH:21][C:19]4[NH:20][C:16]([C:3]5[CH:4]=[C:5]([C:8]6[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=6)[CH:6]=[CH:7][C:2]=5[OH:1])=[N:17][C:18]=4[CH:24]=3)=[O:27])=[CH:46][CH:47]=2)[CH2:36][CH2:35]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 214216774-[2-(4-Pyridin-2-yl-piperazin-1-yl)-ethyl]-phenylamineHCID 1361063252-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid

Produkt 1

HCID 178494101HCID 178494101, VerbindungAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid (containing 1 equivalent of DMA, 44 mg, 0.1 mmol), 4-[2-(4-pyridin-2-yl-piperazin-1-yl)-ethyl]-phenylamine (28.2 mg, 0.1 mmol) and HATU (38 mg, 0.1 mmol) in DMF (1.2 mL) was added DIEA (45 mg, 0.35 mmol). The reaction mixture was stirred at room temperature for 2 h and heated at 60° C. for 3 h, and then evaporated under reduced pressure. The residue was diluted with DMSO (1.5 mL), filtered and then purified with using HPLC (TFA/H2O/CH3CN) to afford the title compound (26.6 mg, 39%). 1H NMR (MeOH-d4) δ 3.10-4.01 (12H), 3.98 (s, 3H), 6.87 (m, 1H), 7.04-7.12 (2H), 7.21 (d, J=9 Hz, 1H), 7.36 (d, J=6 Hz, 2H), 7.72-7.83 (5H), 7.89 (d, J=6 Hz, 1H), 8.09 (d, J=6 Hz, 1H), 8.17 (t, J=3 Hz, 2H), 8.26 (s, 1H), 8.37 (s, 1H). ESI-MS m/z 626.5 (MH+).

Aufarbeitung

  1. temperatureheated at 60° C. for 3 h
  2. customevaporated under reduced pressure
  3. additionThe residue was diluted with DMSO (1.5 mL)
  4. filtrationfiltered
  5. custompurified with using HPLC (TFA/H2O/CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-8ea40e3bbcf6497ba31a89251471ed3f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629147B2

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