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Triethylamine → n-[6-(3-Methyl-3h-[1,2,3]triazol-4-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl]-methanesulfonamide

HRID 906586
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 906586
CO[C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]2[N:11]([CH3:15])[N:12]=[N:13][CH:14]=2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH2:20].CC[N:24]([CH2:27]C)CC.[CH3:29][S:30]([NH:33]N)(=[O:32])=[O:31].[OH-:35].[Na+]>C(Cl)Cl>[CH3:15][N:11]1[C:10]([C:8]2[CH:9]=[C:4]3[C:5](=[CH:6][C:7]=2[C:16]([F:19])([F:17])[F:18])[NH:20][C:27](=[O:35])[N:24]([NH:33][S:30]([CH3:29])(=[O:32])=[O:31])[C:3]3=[O:21])=[CH:14][N:13]=[N:12]1
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 269268MethanesulfonohydrazideHCID 591644362-Amino-5-(3-methyl-3H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester

Produkt 1

HCID 59164524n-[6-(3-Methyl-3h-[1,2,3]triazol-4-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2h-quinazolin-3-yl]-methanesulfonamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-5-(3-methyl-3H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester (357 mg, 1.19 mmol) in DCM (20 mL) were added Et3N (0.67 mL, 4.76 mmol) and then (CCl3O)2CO (288 mg, 0.95 mmol). The resulting mixture was stirred at r.t. for 3 h. The solvent was removed in vacuo and the residue was solubilised in THF. CH3SO2NHNH2 (170 mg, 1.54 mmol) was added and the mixture was stirred at r.t. for 2.5 h. Then, aq NaOH (1N, 1.6 mL) was added and the mixture was stirred for 30 min. The solvent was removed in vacuo and water was added. The pH was adjusted to 2-3 by addition of 1N aq HCl. The aqueous phase was extracted with AcOEt (2×). The organic phases were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a yellow syrup. The yellow syrup was dissolved in DCM (2 mL). Hexanes (8 mL) was added and the resulting precipitate was filtered off, washed with hexanes and dried to afford the title compound as a grey powder (213 mg, 44%). ES-MS: m/z 405.3 [M+CH3CN+H]+, rt 4.1 min. 1H-NMR (DMSO-d6, 400 MHz) 12.16 (s, 1H), 10.40 (s, 1H), 8.11 (s, 1H), 7.77 (s, 1H), 7.68 (s, 1), 3.79 (s, 3H), 3.16 (s, 3H).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. stirringthe mixture was stirred at r.t. for 2.5 h
  3. stirringthe mixture was stirred for 30 min
  4. customThe solvent was removed in vacuo and water
  5. additionwas added
  6. additionThe pH was adjusted to 2-3 by addition of 1N aq HCl
  7. extractionThe aqueous phase was extracted with AcOEt (2×)
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customto afford a yellow syrup
  12. filtrationthe resulting precipitate was filtered off
  13. washwashed with hexanes
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c22c8b5e8558431fbf694b0c4f477875
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012988B2

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