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Diethylethanolamine → HCID 178510407, Verbindung

HRID 1445188
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1445188
[K+].[N:2]1([CH2:8][CH2:9][C:10]([O-:12])=O)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C(OC(=O)CCN1CCOCC1)C.FC(F)(F)C(O)=O.[C:33]1([C:39]2[CH:44]=[C:43]([CH:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[CH:42]=[CH:41][C:40]=2[NH:51][C:52]([C:54]2[NH:55][CH:56]=[C:57]([C:59]#[N:60])[N:58]=2)=[O:53])[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CCO)CC>O.CN(C=O)C>[C:33]1([C:39]2[CH:44]=[C:43]([CH:45]3[CH2:46][CH2:47][N:48]([C:10](=[O:12])[CH2:9][CH2:8][N:2]4[CH2:3][CH2:4][O:5][CH2:6][CH2:7]4)[CH2:49][CH2:50]3)[CH:42]=[CH:41][C:40]=2[NH:51][C:52]([C:54]2[NH:55][CH:56]=[C:57]([C:59]#[N:60])[N:58]=2)=[O:53])[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 7497DiethylethanolamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 88374Ethyl 4-morpholinepropionateHCID 68439679Potassium 3-morpholin-4-ylpropanoateHCID 1785103834-Cyano-1h-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

Produkt 1

HCID 178510407HCID 178510407, VerbindungAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a flask containing 3-morpholin-4-yl-propionic acid potassium salt (94 mg, 0.47 mmol, prepared from 3-morpholin-4-yl-propionic acid ethyl ester exactly as described in Example 7, 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt (179 mg, 0.36 mmol, as prepared in Example 14 (b)), EDCI (83 mg, 0.43 mmol), and HOBT (68 mg, 0.5 mmol) was added DMF (4 mL). To the stirred slurry was added DEEA (157 μL, 0.9 mmol) and the reaction was allowed to stir overnight. The reaction was diluted with H2O (10 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried (Na2SO4), concentrated in vacuo and the crude product was purified by silica gel preparative TLC to afford 10.4 mg (6%) of the title compound as a white solid. 1H-NMR (CDCl3; 400 MHz): δ 1.49-1.93 (m, 5H), 2.22-2.31 (m, 3H), 2.52 (br s, 4H), 2.58-2.63 (m, 3H), 2.74-2.76 (m, 4H), 3.10-3.17 (m, 2H), 3.72 (br s, 4H), 3.97-4.02 (m, 2H), 4.76-4.81 (m, 2H), 5.81-5.82 (m, 1H), 6.81-6.82 (m, 1H), 6.99-7.00 (m, 1H), 7.09-7.13 (m, 1H), 7.70 (s, 1H), 8.26 (d, 1H, J=8.2 Hz), 9.51 (s, 1H); Mass spectrum (ESI, m/z): Calcd. for C29H36N6O3, 517.28 M+H), found 517.3.

Aufarbeitung

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe crude product was purified by silica gel preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-d65e4a97812d40afbda94c1935f99334
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07662837B2

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