Hydrochloric Acid → N-(1-methyl-1-phenylethyl)-3-[(thiophene-3-carbonyl)amino]-1H-pyrazolo[4,3-d]thiazole-5-carboxamide

HRID 501233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501233
[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]([C:31]3[CH:35]=[CH:34][S:33][CH:32]=3)=[O:30])[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]([C:31]3[CH:35]=[CH:34][S:33][CH:32]=3)=[O:30])[C:16]=2[N:17]=1)=[O:12])([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:1]

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 5234Sodium ChlorideHCID 68464926tert-butyl 5-(1-methyl-1-phenylethylcarbamoyl)-3-[(thiophene-3-carbonyl)amino]-1H-pyrazolo[4,3-d]thiazole-1-carboxylate

Produkt 1

HCID 178457750N-(1-methyl-1-phenylethyl)-3-[(thiophene-3-carbonyl)amino]-1H-pyrazolo[4,3-d]thiazole-5-carboxamideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

0.16 g (0.32 mmol) of tert-butyl 5-(1-methyl-1-phenylethylcarbamoyl)-3-[(thiophene-3-carbonyl)amino]-1H-pyrazolo[4,3-d]thiazole-1-carboxylate dissolved in 7 ml of ethanol is placed in a 100 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 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 30 ml of dichloromethane and 30 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 residue is purified by flash chromatography (msilica=30 g; eluent: 95/5 dichloromethane/methanol). 0.104 g of N-(1-methyl-1-phenylethyl)-3-[(thiophene-3-carbonyl)amino]-1H-pyrazolo[4,3-d]thiazole-5-carboxamide is thus obtained in the form of a cream-coloured foam. m.p.K=221° C. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.70 (s, 6H); 7.20 (t, J=7.5 Hz, 1H); 7.31 (t, J=7.5 Hz, 2H); 7.41 (d, J=7.5 Hz, 2H); 7.69 (m, 2H); 8.46 (broad s, 1H); 8.53 (broad s, 1H); from 10.0 to 15.0 (very broad m, 2H).

Aufarbeitung

  1. customis placed in a 100 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 residue is purified by flash chromatography (msilica=30 g; eluent: 95/5 dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-6ac714f4a8884b6b8b000cbe81e4d8df
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772261B2

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