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Acetic Acid → HCID 44243038, Verbindung

HRID 1013090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1013090
OC(C(F)(F)F)=O.[NH2:8][C:9]1([C:32]([NH2:34])=[O:33])[CH2:14][CH2:13][N:12]([C:15]([C:17]2[C:18]3[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=3[S:20][C:21]=2[NH:22][C:23]([NH:25][CH2:26][CH3:27])=[O:24])=[O:16])[CH2:11][CH2:10]1.C(O)(=O)C.[CH2:39]([O:41][C:42](OCC)([O:50]CC)[CH2:43][CH2:44][C:45](OCC)=O)[CH3:40]>C1(C)C=CC=CC=1.CN(C=O)C>[CH2:26]([NH:25][C:23](=[O:24])[NH:22][C:21]1[S:20][C:19]2[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=2[C:17]=1[C:15]([N:12]1[CH2:11][CH2:10][C:9]2([N:8]=[C:45]([CH2:44][CH2:43][C:42]([O:41][CH2:39][CH3:40])=[O:50])[NH:34][C:32]2=[O:33])[CH2:14][CH2:13]1)=[O:16])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 13452377Ethyl 4,4,4-triethoxybutanoateHCID 44243036HCID 44243036, Verbindung

Produkt 1

HCID 44243038HCID 44243038, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel
HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

4-Amino-1-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)piperidine-4-carboxamide (7, 100 mg, 1.0 equivalent) as prepared in Example 7 was dissolved in toluene (0.09 M) and DMF (0.26 M), and to which acetic acid (2.0 equivalents), and ethyl 4,4,4-triethoxybutanoate (4.0 equivalents) were added and the reaction mixture was heated to 85° C. for 9 hrs. The reaction mixture was then partitioned between ethyl acetate and water and the separated organics was washed with brine and dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography (5%-10% MeOH/CH2Cl2 gradient) to afford ethyl 3-(8-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-2-yl)propanoate (10, 65%). Two rotamers observed (ratio 1.3:1).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washthe separated organics was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by SiO2 chromatography (5%-10% MeOH/CH2Cl2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5c8e6aa685ce424e95a19a6b0660754c
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981904B2

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