Phenol → Thieno(3,2-B)pyridine-2-sulfonic acid (1-(1-amino-isoquinolin-7-ylmethyl)-2-oxo-pyrroldin-3-YL)-amide

HRID 394612

Reaktionsgleichung

Reaktionsgleichung von HRID 394612
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]4[S:30][C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:31])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1(O)C=CC=CC=1.C([O-])(=O)C.[NH4+:43]>>[NH2:43][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]4[S:30][C:29]5[C:24](=[N:25][CH:26]=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:31])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 3

HCID 996PhenolHCID 517165Ammonium Acetate2×HCID 53899839Thieno[3,2-b]pyridine-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

Produkt 1

HCID 445480Thieno(3,2-B)pyridine-2-sulfonic acid (1-(1-amino-isoquinolin-7-ylmethyl)-2-oxo-pyrroldin-3-YL)-amide

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Thieno[3,2-b]pyridine-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (1.36 g, 2.88 mmol) and phenol (2.22 g, 23.6 mmol) are melted together with stirring at 70° C. for 5 minutes. Ammonium acetate (2.71 g, 28.8 mmol) is added and the reaction mixture is heated to 90° C. and stirred overnight. Additional ammonium acetate (0.50 g, 5.31 mmol) is added and the reaction is heated for 20 more hours. The reaction is cooled and the residue is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN. The appropriate product fractions are lyophilized to provide the title compound as a white solid. The enantiomeric purity is 90.5% ee as determined by analytical Chiralpak AS RP-HPLC.

Aufarbeitung

  1. temperaturethe reaction mixture is heated to 90° C.
  2. stirringstirred overnight
  3. temperaturethe reaction is heated for 20 more hours
  4. temperatureThe reaction is cooled
  5. customthe residue is purified by RP-HPLC
  6. washeluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Quellen und Nachweise

ORD-Eintrag
ord-4b08a39c19514e579dc74e97f14960ea
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602864B1

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