Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate

HRID 2170138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170138
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]([O:15][CH3:16])=[O:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:41]([C:45]1[CH:46]=[N:47][CH:48]=[C:49]([CH:53]=1)[C:50](O)=[O:51])(=[O:44])(=[O:43])[NH2:42]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:7]1([C:4]2[CH:5]=[CH:6][N:2]([NH:1][C:50](=[O:51])[C:49]3[CH:53]=[C:45]([S:41](=[O:43])(=[O:44])[NH2:42])[CH:46]=[N:47][CH:48]=3)[C:3]=2[C:13]([O:15][CH3:16])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534853495-Sulfamoylpyridine-3-carboxylic acidHCID 90386150HCID 90386150, Verbindung

Produkt 1

HCID 90386125methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylateAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of methyl 1-amino-3-phenyl-1H-pyrrole-2-carboxylate (2.00 g, 9.25 mmol) in DMF (20 mL) was added DMAP (3.39 g, 27.7 mmol) and HATU (10.6 g, 27.7 mmol). The reaction mixture was stirred for 15 minutes and a solution of 5-sulfamoylnicotinic acid (3.74 g, 18.5 mmol) dissolved in DMF was added. The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure to remove DMF and saturated solution of citric acid was added to the residue until the pH was 3. The solution was extracted with CH2Cl2 and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, neutral alumina, 40 g, 13% methanol in CH2Cl2) to afford methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate (1.20 g, 32.4%). LCMS Condition B-39: retention time 1.79 min, [M−1]=399.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.54 (s, 3H), 6.34 (d, J=3.2 Hz, 1H), 7.32-7.44 (m, 7H), 7.80 (br s, 2H), 8.68 (t, J=2.0 Hz, 1H), 9.20 (d, J=2.0 Hz, 1H), 9.30 (d, J=2.0 Hz, 1H).

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 14 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto remove DMF and saturated solution of citric acid
  5. additionwas added to the residue until the pH was 3
  6. extractionThe solution was extracted with CH2Cl2
  7. customthe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c2dcebf59e65442ab78d75c43f1213b3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050345B2

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