Ammonium trifluoroacetate → 2-(5-benzo[b]thiophen-3-yl-1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole

HRID 1244335Notes

Reaction equation

HRID 1244335 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=O)[CH2:7][NH:8][C:9]([C:11]2[S:12][C:13]3[C:19]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=3[N:15]=2)=O)[C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2.FC(F)(F)C([O-])=O.[NH4+:40]>O>[S:1]1[CH:5]=[C:4]([C:6]2[NH:40][C:9]([C:11]3[S:12][C:13]4[C:19]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=4[N:15]=3)=[N:8][CH:7]=2)[C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 865950044-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-benzo[b]thiophen-3-yl-2-oxo-ethyl)-amide

Product 1

HCID 113283652-(5-benzo[b]thiophen-3-yl-1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazoleYield 69.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.15 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-benzo[b]thiophen-3-yl-2-oxo-ethyl)-amide and 0.43 g ammonium triflouroacetate was melted at 210° C. for 30 minutes and, after cooling to room temperature, suspended in water. Extraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1 gave 0.10 g (69%) 2-(5-benzo[b]thiophen-3-yl-1H-imidazol-2-yl)-4-methoxy-7-morpholin-4-yl-benzothiazole as yellow solid; M.p.: 161–162° C.; MS (ISP): m/e=449 (M+H+).

Workup

  1. customfor 30 minutes
  2. extractionExtraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1

Sources & evidence

ORD record
ord-c8c6be1578e54cabadd8aa25314e4009
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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