Trifluoroacetic acid → 1-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone

HRID 133523Notes

Reaction equation

HRID 133523 reaction equation
C(OC([N:8]1[CH2:20][C:19]2[S:18][C:17]3[N:16]=[C:15]([CH3:21])[C:14]([C:22](=[O:24])[CH3:23])=[C:13]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:12]=3[C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH3:21][C:15]1[C:14]([C:22](=[O:24])[CH3:23])=[C:13]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[C:11]3[CH2:10][CH2:9][NH:8][CH2:20][C:19]=3[S:18][C:17]=2[N:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 688966373-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester

Product 1

HCID 688965541-(2-Methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanoneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 70 mg (0.16 mmol) 3-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester in 3 ml dicloromethane was added 0.2 ml trifluoroacetic acid. The mixture was stirred over night at RT, and then poured onto an aqueous solution of NaHCO3, and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford 48 mg (94%) 1-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-ethanone as a yellow solid. ES-MS m/e (%): 323 (M+H+, 100).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b368ea49bb76499ba70b43c500e1adde
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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