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Triethylamine → 3-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

HRID 1663155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1663155
[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.C(N(CC)CC)C.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.Cl.[CH3:50][C:51]1[S:52][CH:53]=[C:54]([CH2:56][O:57][NH2:58])[N:55]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:58][O:57][CH2:56][C:54]1[N:55]=[C:51]([CH3:50])[S:52][CH:53]=1)=[O:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 54606663HCID 54606663, VerbindungHCID 589898483-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid

Produkt 1

HCID 112228443-Methoxy-N-(2-methyl-thiazol-4-ylmethoxy)-2-[(pyridin-4-ylmethyl)-amino]-benzamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Methoxy-2-[(pyridin-4-ylmethyl)-amino]-benzoic acid (200 mg, see preparation 1D) was dissolved in DMF (20 ml) and triethylamine (0.65 ml) at 50-60° C. N,N,N′,N′-Tetramethyl-O-(benzotriazole-1-yl)uronium-tetrafluoroborate (250 mg) was added and after 5 minutes O-(2-methyl-thiazol-4-ylmethyl)-hydroxylamine hydrochloride (209 mg, see preparation 12) was added. The reaction mixture was heated to 90° C. and stirred at this temperature for 2 hours. The mixture was cooled to room temperature and water was added. The mixture was extracted several times with EtOAc and the combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc) and gave the title compound as an yellow oil. 13C-NMR (DMSO-d6) δ 165.3, 150.4, 150.0, 149.8, 149.3, 137.8, 122.2, 120.5, 118.8, 117.9, 114.0, 71.8, 55.7, 48.3, 18.6.

Aufarbeitung

  1. customat 50-60° C
  2. additionwas added
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted several times with EtOAc
  5. washthe combined organic layers were washed with water, saturated aqueous sodium bicarbonate, water, and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe remaining material was purified by column chromatography on silica gel (elution with 1 to 4% methanol in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4a54bf290030467893716d7e6663d365
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08034811B2

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