4-(Pyridin-2-yl)-1,3-thiazol-2-amine → 4-(N-(4-fluorophenyl)-N-methylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide

HRID 1397910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397910
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:21])[S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:33][C:30]3[S:31][CH:32]=[C:28]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=4)[N:29]=3)=[O:18])=[CH:19][CH:20]=2)(=[O:10])=[O:11])=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 10924594-(Pyridin-2-yl)-1,3-thiazol-2-amineHCID 566871464-(N-(4-fluorophenyl)-N-methylsulfamoyl)benzoic acid

Produkt 1

HCID 469126834-(N-(4-fluorophenyl)-N-methylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide

Versuchsvorschrift

4-(N-(4-fluorophenyl)-N-methylsulfamoyl)benzoic acid (4) (100 mg, 0.32 mmol) was treated with 4-(pyridin-2-yl)thiazol-2-amine (48 mg, 0.27 mmol) using method C. The residue was purified using flash chromatography eluting with EtOAc. The resulting solid was triturated with diethyl ether to give 4-(N-(4-fluorophenyl)-N-methylsulfamoyl)-N-(4-(pyridin-2-yl)thiazol-2-yl)benzamide as a yellow solid. Yield: 34 mg (27%). 1H-NMR: 8.61 (d, J=4.5 Hz, 1H), 8.29 (d, J=8.5 Hz, 2H), 8.02 (d, J=8.5 Hz, 1H), 7.93-7.83 (m, 2H), 7.65 (d, J=8.5 Hz, 2H), 7.36-7.31 (m, 1H), 7.24-7.12 (m, 4H), 3.17 (s, 3H).

Aufarbeitung

  1. customThe residue was purified
  2. washeluting with EtOAc
  3. customThe resulting solid was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-01d79d445fd949739d9787997fdcb4fe
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901306B2

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