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Hydrochloric Acid → HCID 178457749, Verbindung

HRID 501229
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 501229
[CH3:1][C:2]([NH:10][C:11]([C:13]1[S:14][C:15]2[N:20](C(OC(C)(C)C)=O)[N:19]=[C:18]([NH:28][C:29](=[O:42])[C:30]3[CH:35]=[CH:34][C:33]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:32][CH:31]=3)[C:16]=2[N:17]=1)=[O:12])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].Cl.[Cl-].[Na+]>C(O)C.O1CCOCC1>[CH3:3][C:2]([NH:10][C:11]([C:13]1[S:14][C:15]2[NH:20][N:19]=[C:18]([NH:28][C:29](=[O:42])[C:30]3[CH:35]=[CH:34][C:33]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:32][CH:31]=3)[C:16]=2[N:17]=1)=[O:12])([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:1]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 5234Sodium ChlorideHCID 68462978tert-butyl 5-(1-methyl-1-phenylethylcarbamoyl)-3-(4-morpholin-4-ylbenzoylamino)-1H-pyrazolo[4,3-d]thiazole-1-carboxylate

Produkt 1

HCID 178457749HCID 178457749, VerbindungAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

0.19 g (0.32 mmol) of tert-butyl 5-(1-methyl-1-phenylethylcarbamoyl)-3-(4-morpholin-4-ylbenzoylamino)-1H-pyrazolo[4,3-d]thiazole-1-carboxylate dissolved in 7 ml of ethanol is placed in a 50 ml round-bottomed flask. 1.6 ml (6.4 mmol) of a 4M solution of hydrochloric acid in dioxane are then added and the reaction mixture is stirred for 15 hours at 25° C. A further 1.6 ml (6.4 mmol) of a 4M solution of hydrochloric acid in dioxane are then added and the mixture is stirred for 15 hours at 25° C. The reaction medium is then concentrated to dryness under reduced pressure (40° C.) and the residue is taken up in 40 ml of dichloromethane and 40 ml of water, and basified with 0.1N sodium hydroxide solution. The emulsion obtained is resorbed by saturation with sodium chloride. After separation of the phases by settling, the organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure (40° C.). The yellow residue is purified by flash chromatography (msilica=30 g; eluent: 97/3 dichloromethane/methanol). 0.097 g of N-(1-methyl-1-phenylethyl)-3-(4-morpholin-4-ylbenzoylamino)-1H-pyrazolo[4,3-d]thiazole-5-carboxamide is thus obtained in the form of a yellow foam. m.p.K=266° C. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.70 (s, 6H); 3.29 (masked m, 4H); 3.75 (m, 4H); 7.04 (d, J=8.5 Hz, 2H); 7.20 (t, J=7.5 Hz, 1H); 7.31 (t, J=7.5 Hz, 2H); 7.41 (d, J=7.5 Hz, 2H); 7.99 (d, J=8.5 Hz, 2H); 8.50 (broad s, 1H); 10.8 (broad m, 1H); 13.6 (broad m, 1H).

Aufarbeitung

  1. customis placed in a 50 ml round-bottomed flask
  2. stirringthe mixture is stirred for 15 hours at 25° C
  3. concentrationThe reaction medium is then concentrated to dryness under reduced pressure (40° C.)
  4. customThe emulsion obtained
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure (40° C.)
  8. customThe yellow residue is purified by flash chromatography (msilica=30 g; eluent: 97/3 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-5f9af2525ce448ab9b3cb70afd573254
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772261B2

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