Potassium Phosphate, Tribasic → N-(4-[{3-(Dimethylamino)pyrrolidin-1-yl]carbonyl}phenyl)-2,1,3-benzothiadiazol-4-amine

HRID 1176062

Reaktionsgleichung

Reaktionsgleichung von HRID 1176062
Br[C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:27]2[C:23](=[N:24][S:25][N:26]=2)[CH:22]=[CH:21][CH:20]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.C1C=CC([C]2[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C]2C2C=CC=CC=2)=CC=1.[Fe]>[CH3:14][N:13]([CH3:15])[CH:10]1[CH2:11][CH2:12][N:8]([C:6]([C:5]2[CH:16]=[CH:17][C:2]([NH:18][C:19]3[C:27]4[C:23](=[N:24][S:25][N:26]=4)[CH:22]=[CH:21][CH:20]=3)=[CH:3][CH:4]=2)=[O:7])[CH2:9]1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 698452,1,3-Benzothiadiazol-4-amineHCID 590120191-(4-Bromobenzoyl)-3-dimethylaminopyrrolidine

Produkt 1

HCID 24794880N-(4-[{3-(Dimethylamino)pyrrolidin-1-yl]carbonyl}phenyl)-2,1,3-benzothiadiazol-4-amineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 178454872HCID 178454872, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-(4-bromobenzoyl)-3-dimethylaminopyrrolidine (40 mg, 0.13 mmol), 4-amino-2,1,3-benzothiadiazole (23 mg, 0.13 mmol), potassium phosphate (27 mg, 0.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (3 mg, 0.002 mmol), and CTC-Q-Phos (6 mg, 0.004 mmol) are heated to 80° C. for 16 h and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, methanol and water and purified by reverse-phase semi-preparative HPLC1 to give the title compound as a white powder (11 mg), identified by HPLC and mass spectral analyses. Retention Time, 1.74 min.; MS [368.6 m/e (M+H)]. 1Semi-preparative HPLC Conditions: A=0.02% TFA in water, B=0.02% TFA in acetonitrile, 10-95% B in 8 min., 34 mL/min, 50° C., 215 nm detection, Waters Xterra™ 20×50 mm column.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of DMSO, methanol and water
  3. custompurified by reverse-phase semi-preparative HPLC1

Quellen und Nachweise

ORD-Eintrag
ord-130dd92dfc9f4d21ad3057123619425e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842715B2

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