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2-Methoxyethylamine → 1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[6-(2-methoxy-ethylsulfamoyl)-pyridin-3-ylmethyl]-amide

HRID 2198099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2198099
COC(=O)CC[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])=[CH:11][N:10]=1)(=[O:8])=[O:7].[O-]CC.[Na+].ClN1C(=O)CCC1=O.[CH3:48][O:49][CH2:50][CH2:51][NH2:52]>C1COCC1.C(O)C.[Cl-].[NH4+].CCOC(C)=O>[CH3:48][O:49][CH2:50][CH2:51][NH:52][S:6]([C:9]1[N:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])=[CH:13][CH:14]=1)(=[O:7])=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 80182-MethoxyethylamineHCID 31398ChlorosuccinimideHCID 2723922Sodium ethoxideHCID 592783133-[5-({[1-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-propionic acid methyl ester

Produkt 1

HCID 592783991-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid[6-(2-methoxy-ethylsulfamoyl)-pyridin-3-ylmethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 3-[5-({[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-propionic acid methyl ester (100 mg, 0.2 mmol) in THF (5 mL) was added a freshly prepared 8% solution of sodium ethoxide (200 μL, 0.2 mmol) in ethanol. The mixture was stirred for 15 minutes and was monitored for the disappearance of starting material by TLC (EtOAc). The mixture was then concentrated to dryness under a stream of nitrogen. The mixture was again diluted with THF and then N-chlorosuccinimide (55 mg, 0.41 mmol) was added. After 15 minutes, 2-methoxyethylamine (0.100 mL, 1.15 mmol) was added in one portion. After 15 minutes, the mixture was diluted with saturated ammonium chloride and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (2×10 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with methanol-EtOAc (0:100, then 0.5:99.5, then 1:99, then 2:98). The material from the column was purified a second time by using preparative silica gel TLC eluting with methanol-EtOAc (1:9). The material from the plate was triturated with EtOAc-ether-hexanes to afford the title compound.

Aufarbeitung

  1. concentrationThe mixture was then concentrated to dryness under a stream of nitrogen
  2. additionThe mixture was again diluted with THF
  3. waitAfter 15 minutes
  4. waitAfter 15 minutes
  5. extractionextracted with EtOAc (3×10 mL)
  6. washThe combined organic layers were washed with brine (2×10 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was purified by silica gel chromatography
  11. washeluting with methanol-EtOAc (0:100
  12. customThe material from the column was purified a second time
  13. washeluting with methanol-EtOAc (1:9)
  14. customThe material from the plate was triturated with EtOAc-ether-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-232218545b994e689bf694f218bd2ee7
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08338610B2

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