1,2-Dichloroethane → HCID 86632320, Verbindung

HRID 1695946

Reaktionsgleichung

Reaktionsgleichung von HRID 1695946
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20](=[O:28])[CH:19]([CH2:29][C:30]([OH:32])=O)[S:18]2)[CH2:3][CH2:2]1.[NH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:47]3[C:42](=[N:43][CH:44]=[CH:45][CH:46]=3)[NH:41][C:40]2=[O:48])[CH2:35][CH2:34]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:20](=[O:28])[C@H:19]([CH2:29][C:30]([N:33]3[CH2:34][CH2:35][CH:36]([N:39]4[C:47]5[C:42](=[N:43][CH:44]=[CH:45][CH:46]=5)[NH:41][C:40]4=[O:48])[CH2:37][CH2:38]3)=[O:32])[S:18]2)[CH2:5][CH2:6]1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 866323182-(2-(2-(2-Morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

Produkt 1

HCID 86632320HCID 86632320, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(2-(2-(2-Morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (420.8 mg, 0.9 mmol), 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (545 mg, 1.872 mmol), EDC (360 mg, 1.878 mmol), HOBt (282 mg, 1.841 mmol) and DIEA (730 μL, 4.191 mmol) were stirred in DMF (6 mL) at RT. The mixture was diluted with EtOAc and washed with water and saturated sodium bicarbonate solution. The aqueous layer was back-extracted, the organic layers were combined, then washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product was purified by reverse phase column chromatography with ACN/water to give 1-(1-(2-((5S)-2-(2-(2-morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Aufarbeitung

  1. washwashed with water and saturated sodium bicarbonate solution
  2. extractionThe aqueous layer was back-extracted
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase column chromatography with ACN/water

Quellen und Nachweise

ORD-Eintrag
ord-18127d41996048e5b0a81fa954c07f88
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163737B2

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