Ammonium trifluoroacetate → 4-methoxy-7-morpholin-4-yl-2-(4,5,6,7-tetrahydro-1H-benzoimidazol-2-yl)-benzothiazole

HRID 1244347Notes

Reaction equation

HRID 1244347 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][C:9]([C:11]1[S:12][C:13]2[C:19]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=2[N:15]=1)=O.FC(F)(F)C([O-])=O.[NH4+:35]>O>[CH3:27][O:26][C:16]1[C:14]2[N:15]=[C:11]([C:9]3[NH:35][C:2]4[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=4[N:8]=3)[S:12][C:13]=2[C:19]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 865950064-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-cyclohexyl)-amide

Product 1

HCID 113147054-methoxy-7-morpholin-4-yl-2-(4,5,6,7-tetrahydro-1H-benzoimidazol-2-yl)-benzothiazoleYield 42.1%

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-cyclohexyl)-amide and 0.34 g ammonium triflouroacetate was melted at 165° C. for 50 minutes and, after cooling to room temperature, suspended in water. Extraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 6:4 gave 0.04 g (39%) 4-methoxy-7-morpholin-4-yl-2-(4,5,6,7-tetrahydro-1H-benzoimidazol-2-yl)-benzothiazole as light brown solid; MS (ISP): m/e=371 (M+H+).

Workup

  1. customfor 50 minutes
  2. extractionExtraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 6:4

Sources & evidence

ORD record
ord-6675db5f0e4c45d88956656b2ddf595a
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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