Ammonium trifluoroacetate → 4-methoxy-7-morpholin-4-yl-2-(4-thiophen-3-yl-1H-imidazol-2-yl)-benzothiazole

HRID 1244339Notes

Reaction equation

HRID 1244339 reaction equation
O=[C:2]([C:24]1[CH:28]=[CH:27][S:26][CH:25]=1)[CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]2[C:15]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:14][CH:13]=[C:12]([O:22][CH3:23])[C:10]=2[N:11]=1)=O.FC(F)(F)C([O-])=O.[NH4+:36]>O>[CH3:23][O:22][C:12]1[C:10]2[N:11]=[C:7]([C:5]3[NH:4][CH:3]=[C:2]([C:24]4[CH:28]=[CH:27][S:26][CH:25]=4)[N:36]=3)[S:8][C:9]=2[C:15]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 211370574-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-3-yl-ethyl)-amide

Product 1

HCID 1784920134-methoxy-7-morpholin-4-yl-2-(4-thiophen-3-yl-1H-imidazol-2-yl)-benzothiazoleYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.10 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-3-yl-ethyl)-amide and 0.32 g ammonium triflouroacetate was melted at 170° C. for 50 minutes and, after cooling to room temperature, suspended in water. Extraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1 gave 0.06 g (59%) 4-methoxy-7-morpholin-4-yl-2-(4-thiophen-3-yl-1H-imidazol-2-yl)-benzothiazole as yellow solid; MS (ISP): m/e=399 (M+H+).

Workup

  1. customfor 50 minutes
  2. extractionExtraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1

Sources & evidence

ORD record
ord-1ae9d2c5cefa4a5fa8a843cfc042200e
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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