Ammonium trifluoroacetate → HCID 178492010, compound

HRID 1244333Notes

Reaction equation

HRID 1244333 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=O)[CH2:12][NH:13][C:14]([C:16]3[S:17][C:18]4[C:24]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[CH:23][CH:22]=[C:21]([O:31][CH3:32])[C:19]=4[N:20]=3)=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.FC(F)(F)C([O-])=O.[NH4+:41]>O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:41]=[C:14]([C:16]4[S:17][C:18]5[C:24]([N:25]6[CH2:30][CH2:29][O:28][CH2:27][CH2:26]6)=[CH:23][CH:22]=[C:21]([O:31][CH3:32])[C:19]=5[N:20]=4)[NH:13][CH:12]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 21137090HCID 21137090, compound

Product 1

HCID 178492010HCID 178492010, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.19 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-ethyl]-amide and 0.54 g ammonium triflouroacetate was melted at 175° C. for 45 minutes and, after cooling to room temperature, suspended in water. Extraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 6:4 gave 0.13 g (71%) 2-[4-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1H-imidazol-2-yl]-4-methoxy-7-morpholin-4-yl-benzothiazole as yellow solid; M.p.: 235–237° C.; MS (ISP): m/e=451 (M+H+).

Workup

  1. customfor 45 minutes
  2. extractionExtraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 6:4

Sources & evidence

ORD record
ord-8734ec1d4e9b4077b733e65b79bd5d34
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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