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N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178474439, Verbindung

HRID 1246492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1246492
[C:1]([NH:4][C:5]1[S:6][C:7]([C:19]([OH:21])=[O:20])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[C:34]([O:38][C:39]([NH:41][C:42](N1C=CC=N1)=[N:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]>C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([C:19]([OH:21])=[O:20])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]/[C:42](/[NH:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])=[N:43]/[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 11708267BistrimethylsilylacetamidHCID 219152482-(Acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylic acid

Produkt 1

HCID 178474439HCID 178474439, VerbindungAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

2-(Acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazole-5-carboxylic acid (106 mg) was suspended in THF (2 ml) under N2 atmosphere. Bis(trimethylsilyl)acetamide (0.253 ml) was added to the suspension at r.t., and the mixture was stirred at r.t. for 15 minutes. Then, N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (119 mg) was added to the solution at r.t. The reaction mixture was stirred at r.t. for 20 hours, and concentrated in vacuo. The residue was dissolved in CHCl3. The organic solution was washed with 1N-HCl, water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid was washed with ethyl ether to give 2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino](tert-butoxycarbonyl)iminomethyl}amino)phenyl]ethyl}-1,3-thiazole-5-carboxylic acid (115.8 mg) as a pale brown solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at r.t. for 20 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CHCl3
  4. washThe organic solution was washed with 1N-HCl, water and brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe residual solid was washed with ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2a854a60231e4bfaa55c2d16d8de4724
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07125901B2

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