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4-Hydroxymethylpyridine → Ethyl 3-[{[4-({cyclohexyl[3-methyl-5-(pyridin-4-ylmethoxy)-1-benzofuran-2-yl]methyl}amino)phenyl]carbonyl}(methyl)amino]propanoate

HRID 2091346
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2091346
[CH:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:22][CH:21]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:37]1[CH:42]=[CH:41][C:40]([CH2:43]O)=[CH:39][CH:38]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH:1]1([CH:7]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:36])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:27])=[CH:24][CH:25]=2)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([O:18][CH2:43][C:40]4[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=4)=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 114724-HydroxymethylpyridineHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 66777718HCID 66777718, Verbindung

Produkt 1

HCID 66777901Ethyl 3-[{[4-({cyclohexyl[3-methyl-5-(pyridin-4-ylmethoxy)-1-benzofuran-2-yl]methyl}amino)phenyl]carbonyl}(methyl)amino]propanoateAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 3-{[(4-{[cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate (0.23 g) synthesized in Example A155(1) was dissolved in tetrahydrofuran (5 mL), and 4-pyridinemethanol (62 mg), tributylphosphine (0.21 mL) and 1,1′-(azodicarbonyl)dipiperidine (0.21 g) were added to the solution under ice-cooling. The ice bath was removed, the reaction mixture was stirred at room temperature for 12 hr, then hexane (5 mL) was added to the mixture, and the precipitate was filtered off through celite. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio) to give the title object compound (0.18 g, 64%) as a pale-yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. customThe ice bath was removed
  3. additionhexane (5 mL) was added to the mixture
  4. filtrationthe precipitate was filtered off through celite
  5. additionWater was added to the filtrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1, volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-c5eac815c4bc4843a9203a7523410f6d
Quelldatensatz
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08436043B2

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