Trifluoroacetic acid → 7-(2-{[4-(1-Piperazinyl)-1,2,5-thiadiazol-3-yl]oxy}ethoxy)-2H-chromen-2-one

HRID 991700Notes

Reaction equation

HRID 991700 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([O:12][CH2:13][CH2:14][O:15][C:16]3[C:17]([N:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[N:18][S:19][N:20]=3)=[CH:7][CH:8]=2)[O:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[N:21]1([C:17]2[C:16]([O:15][CH2:14][CH2:13][O:12][C:6]3[CH:5]=[C:4]4[C:9]([CH:10]=[CH:11][C:2](=[O:1])[O:3]4)=[CH:8][CH:7]=3)=[N:20][S:19][N:18]=2)[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22036300tert-Butyl 4-(4-{2-[(2-oxo-2H-chromen-7-yl)oxy]ethoxy}-1,2,5-thiadiazol-3-yl)-1-piperazinecarboxylate

Product 1

HCID 220362437-(2-{[4-(1-Piperazinyl)-1,2,5-thiadiazol-3-yl]oxy}ethoxy)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product obtained in Step 3 (176 mg) was diluted in CH2Cl2 (1.5 mL) and cooled to ˜0° C. Trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred for 1 h at 5° C. After solvent removal in vacuo, the residue was purified by chromatography on silica gel using hexane/EtOAc (1:1) followed by CH2Cl2/MeOH/Et3N (90:5:5) as eluents This furnished 45 mg (40%) of the title product as a white solid. MS m/z 375 (M+H)+.

Workup

  1. customAfter solvent removal in vacuo
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-80065f5490fd4fddb22b55173373294d
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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