Dimethylacetamide → HCID 46852596, Verbindung

HRID 400526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400526
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:47]1[NH:52][CH2:51][CH2:50][N:49]2[CH2:53][CH2:54][CH2:55][C@H:48]12.CN(C)C(=O)C>CC1CCCO1>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]([C:4]([N:52]2[CH2:51][CH2:50][N:49]3[CH2:53][CH2:54][CH2:55][C@@H:48]3[CH2:47]2)=[O:6])=[CH:7][C:8]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])(=[O:14])=[O:13]

Komponenten

6

Edukt 4

HCID 31374Dimethylacetamide2×HCID 23243772,4-Dichloro-5-[[(2-fluorophenyl)amino]sulfonyl]benzoic acidHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 46852596HCID 46852596, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73012-MethyltetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 2,4-dichloro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid (800 mg, 2.197 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (919 mg, 2.416 mmol) in 2-methyltetrahydrofuran (15 mL) was added (R)-octahydropyrrolo[1,2-a]pyrazine (388 mg, 3.08 mmol). The reaction was stirred at room temperature for 45 minutes at which time N,N-dimethylacetamide (1 mL) was added. The reaction was stirred for an additional 45 minutes and N,N-dimethylacetamide (3 mL) was added. The reaction was stirred for an addition 2.5 hours, diluted with 2-methyltetrahydrofuran (15 mL), and washed with a solution of 6% sodium bicarbonate and 6% brine (2×15 mL). The aqueous layers were combined and re-extracted with 2-methyltetrahydrofuran (15 mL). The organic layer was washed with saturated brine (4×25 mL), dried over MgSO4, and concentrated. The residue was taken up in ethanol (20 mL) and reconcentrated to give the title compound.

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction was stirred for an addition 2.5 hours
  3. washwashed with a solution of 6% sodium bicarbonate and 6% brine (2×15 mL)
  4. extractionre-extracted with 2-methyltetrahydrofuran (15 mL)
  5. washThe organic layer was washed with saturated brine (4×25 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-584b65f02983455c883a0d3c51251253
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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