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Hexane → HCID 44243040, Verbindung

HRID 1013091
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1013091
CCCCCC.[CH2:7]([N:9]([Al](C)C)[CH2:10][CH3:11])[CH3:8].[CH2:15]([NH:17][C:18](=[O:49])[NH:19][C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[C:21]=1[C:29]([N:31]1[CH2:48][CH2:47][C:34]2([N:38]=[C:37]([CH2:39][CH2:40][C:41]([O:43]CC)=O)[NH:36][C:35]2=[O:46])[CH2:33][CH2:32]1)=[O:30])[CH3:16]>C1C=CC=CC=1.C1COCC1>[CH2:7]([N:9]([CH2:10][CH3:11])[C:41](=[O:43])[CH2:40][CH2:39][C:37]1[NH:36][C:35](=[O:46])[C:34]2([CH2:33][CH2:32][N:31]([C:29]([C:21]3[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[S:24][C:20]=3[NH:19][C:18]([NH:17][CH2:15][CH3:16])=[O:49])=[O:30])[CH2:48][CH2:47]2)[N:38]=1)[CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 16708834HCID 16708834, VerbindungHCID 44243038HCID 44243038, Verbindung

Produkt 1

HCID 44243040HCID 44243040, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a 2.0 M hexane solution of (diethylamino)dimethylaluminum (3.2 equivalents) in dry benzene (0.26 M) was cooled to −15° C., a solution of 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 (Example 10), 12 mg, 1.0 equivalent) in THF (0.16M) was added; the mixture was heated to 80° C. for 6 hrs. The mixture was cooled in an ice bath; then a saturated aqueous Rochelle's solution was added and stirred for 1 hr, 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 preparatory LCMS to afford N,N-diethyl-3-(8-(2-(3-ethylureido)benzo[b]thiophene-3-carbonyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-2-yl)propanamide (10, 20%). Two rotamers observed (ratio 1.3:1).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. additionthen a saturated aqueous Rochelle's solution was added
  3. custompartitioned between ethyl acetate and water
  4. washthe separated organics was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparatory LCMS

Quellen und Nachweise

ORD-Eintrag
ord-1d3b65ccb6564805a438ed9d193f40e5
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07981904B2

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