1,2-Dichloroethane → 1-(cyclopropanecarbonyl)-N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)azetidine-3-carboxamide

HRID 1669955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669955
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:27]=[C:28]([NH:32][C:33]([CH:35]4[CH2:38][NH:37][CH2:36]4)=[O:34])[CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:24])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(O[BH-](O[C:49](=[O:51])[CH3:50])OC(=O)C)(=O)C.C[N+](C)(C)C.Cl[CH2:58][CH2:59]Cl>CN(C=O)C>[CH:50]1([C:49]([N:37]2[CH2:38][CH:35]([C:33]([NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([S:23](=[O:25])(=[O:24])[NH:22][C:13]4[C:12]([NH:11][C:5]5[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=5)=[N:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[CH:27]=3)=[O:34])[CH2:36]2)=[O:51])[CH2:59][CH2:58]1

Komponenten

5

Edukt 3

HCID 111,2-DichloroethaneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 57448472N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)azetidine-3-carboxamide

Produkt 1

HCID 574485091-(cyclopropanecarbonyl)-N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)azetidine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(3-(N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)azetidine-3-carboxamide (110 mg, 0.19 mmol), prepared using procedures similar to those described in Example 372, in 3 mL of DCE and 200 μL of DMF, aldehyde (0.77 mmol, 4.0 eq.)was added slowly followed by tetramethylammonium triacetoxyborohydride (1.16 mmol, 6.0 eq). The reaction was stirred at room temperature overnight. LC/MS indicated the reaction was completed. The solvent was subsequently removed under reduced pressure on a rotary evaporator. The crude material was then redissolved in methanol. Purification of the final product was accomplished by preparatory reverse-phase HPLC with the eluents 25 mM aqueous NH4OAc/CAN. A Waters Fractionlynx preparative reverse-phase HPLC; equipped with a Waters SunFire Prep C18, OCD 5 μM, 30×70 mm column and running a 5-100% gradient with a binary solvent system of 25 mM ammonium acetate in water/acetonitrile; was used to carry out the purification.

Aufarbeitung

  1. customThe solvent was subsequently removed under reduced pressure on a rotary evaporator
  2. dissolutionThe crude material was then redissolved in methanol
  3. customPurification of the final product
  4. customequipped with a Waters SunFire Prep C18, OCD 5 μM, 30×70 mm column
  5. customthe purification

Quellen und Nachweise

ORD-Eintrag
ord-287925fd121f4bf5bfb8407ab222db85
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989622B2

Notizen zur Reaktion

Wird geladen…