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Diisopropylethylamine → HCID 178499687, Verbindung

HRID 1713937
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1713937
FC(F)(F)C([O-])=O.[CH3:8][O:9][C:10](=[O:28])/[CH:11]=[CH:12]/[C:13]1[CH:27]=[CH:26][C:16]2[NH:17][C:18]([C:20]3([NH3+:25])[CH2:24][CH2:23][CH2:22][CH2:21]3)=[N:19][C:15]=2[CH:14]=1.[CH:29]1([C:35]2[C:43]3[C:38](=[CH:39][C:40]([C:44](O)=[O:45])=[CH:41][CH:42]=3)[N:37]([CH2:47][C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:36]=2[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]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>[CH:29]1([C:35]2[C:43]3[C:38](=[CH:39][C:40]([C:44]([NH:25][C:20]4([C:18]5[NH:17][C:16]6[CH:26]=[CH:27][C:13](/[CH:12]=[CH:11]/[C:10]([O:9][CH3:8])=[O:28])=[CH:14][C:15]=6[N:19]=5)[CH2:24][CH2:23][CH2:22][CH2:21]4)=[O:45])=[CH:41][CH:42]=3)[N:37]([CH2:47][C:48]([N:50]([CH3:52])[CH3:51])=[O:49])[C:36]=2[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 52754443-Cyclohexyl-1-dimethylcarbamoylmethyl-2-phenyl-1H-indole-6-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178499688HCID 178499688, Verbindung

Produkt 1

HCID 178499687
HCID 178499687, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-{5-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1H-benzimidazol-2-yl}cyclopentanaminium trifluoroacetate (from Step 4, 1 eq), 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-indole-6-carboxylic acid (from Example 1, Step 6, 1 eq) in DMF (0.02 M), HATU (1 eq) and DIPEA (5 eq) were added. The reaction mixture was left at RT with stirring overnight. The resulting mixture was partitioned between EtOAc and hydrochloric acid. The combined EtOAc layers were washed with saturated aqueous NaCl solution, separated, dried over Na2SO4, filtered and evaporated in vacuo to afford methyl (2E)-3-(2-{1-[({3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-phenyl-1H-indol-6-yl}carbonyl)amino]cyclopentyl}-1H-benzimidazol-5-yl)acrylate, which was used without further purification. MS (ES+) m/z 672 (M+H)+.

Aufarbeitung

  1. waitThe reaction mixture was left at RT
  2. customThe resulting mixture was partitioned between EtOAc and hydrochloric acid
  3. washThe combined EtOAc layers were washed with saturated aqueous NaCl solution
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-530c7cd18162468386e9e6d4a09a08dc
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795250B2

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