Trifluoroacetic acid → HCID 66625538, compound

HRID 1663271Notes

Reaction equation

HRID 1663271 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([NH2:16])[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2].[CH:18]([C:20]1[S:24][C:23]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)=[CH:22][CH:21]=1)=O.C(O)(C(F)(F)F)=O>C(O)(C)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([N:16]=[CH:18][C:20]2[S:24][C:23]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[CH:22][CH:21]=2)[S:8][C:7]=1[NH2:17])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 364428[2,2'-Bithiophene]-5-carboxaldehydeHCID 840025Diethyl 2,5-diaminothiophene-3,4-dicarboxylate

Product 1

HCID 66625538HCID 66625538, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,5-Diamino-thiophene-3,4-dicarboxylic acid diethyl ester (30 mg, 0.25 mmol) was mixed with 5-formyl-2,2′bithiophene (40 mg, 0.25 mmol) in isopropanol and refluxed for five hours following the catalytic addition of TFA. The solvent was removed and the product isolated as a yellow solid after purification by flash chromatography (42 mg, 64%). 1H-NMR (300 MHz, [D] DMSO): δ=8.19 (s, 1H), 7.89 (s, 2H), 7.58 (d, 1H, 3J=5.2 Hz), 7.50 (d, 1H, 3J=3.9 Hz) 7.41 (d, 1H, 3J=3.6 Hz), 7.34 (d, 1H, 3J=3.9 Hz), 7.11 (t, 1H, 3J=3.6 Hz), 4.25 (q, 2H, 3J=7.1 Hz), 4.12 (q, 2H, 3J=7.2 Hz), 1.31 (t, 3H, 3J=7.2 Hz), 1.19 (t, 3H, 3J=7.0 Hz). 13C-NMR (300 MHz, [D] acetone): δ=165.5, 164.8, 161.7, 146.1, 142.3, 141.9, 137.7, 137.6, 133.5, 133.4, 131.1, 129.2, 126.9, 125.8, 125.3, 61.5, 60.5, 14.8, 14.6. EI-MS: m/z 434.9 ([M]+, 96%).

Workup

  1. temperaturerefluxed for five hours
  2. customThe solvent was removed
  3. customthe product isolated as a yellow solid
  4. customafter purification by flash chromatography (42 mg, 64%)

Sources & evidence

ORD record
ord-0b0dd1ecb5db4dcb90e8c01e57e4e762
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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