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Water → tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamate

HRID 459623
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459623
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH:40][C:41](=[O:54])[C:42](=O)[CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[CH:17]=[N:16]1.O>O1CCCC1>[C:1](/[CH:3]=[C:42](/[C:41]([NH:40][C:18]1[CH:17]=[N:16][N:15]([CH3:14])[C:19]=1[NH:20][C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:54])\[CH2:43][CH2:44][NH:45][C:46](=[O:52])[O:47][C:48]([CH3:49])([CH3:51])[CH3:50])#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 86597878tert-butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate

Produkt 1

HCID 86597879tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamate
Ausbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of diethyl (cyanomethyl)phosphonate (704 mg) in tetrahydrofuran (20 ml) was added sodium hydride (159 mg, 60% oil suspension) under ice-cooling. The mixture was stirred for 45 minutes with warming to room temperature. tert-Butyl (4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxobutyl)carbamate (2 g) was added to the mixture, and the whole mixture was stirred at room temperature for 2 hours. Water was added to the mixture, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a residual oil, which was triturated with a small amount of ethyl acetate and diluted with diisopropyl ether. The resulting precipitate was collected by filtration to give tert-butyl [(3E)-4-cyano-3-({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)-3-buten-1-yl]carbamate (1.41 g).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe whole mixture was stirred at room temperature for 2 hours
  3. extractionthe whole mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customto give a residual oil, which
  8. customwas triturated with a small amount of ethyl acetate
  9. additiondiluted with diisopropyl ether
  10. filtrationThe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a2a04bead5ee4113b5640c4f61f770a9
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07192943B2

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