Trifluoroacetic acid → HCID 66625194, compound
Reaction equation
S1C=CC=C1[C:6]1[S:10][C:9]([CH:11]=O)=[CH:8][CH:7]=1.[NH2:13][C:14]1[S:15][C:16]([NH2:29])=[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[C:30](O)([C:32](F)(F)F)=O>C(O)(C)C>[CH2:22]([O:21][C:19]([C:18]1[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:16]([N:29]=[CH:8][C:9]2[S:10][CH:6]=[CH:30][CH:32]=2)[S:15][C:14]=1[N:13]=[CH:11][C:9]1[S:10][CH:6]=[CH:7][CH:8]=1)=[O:20])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
This compound can be synthesized either step-wise or one-pot. Step-wise formation was achieved by adding 5-(thiophen-2-yl)thiophene-2-carbaldehyde (30 mg, 0.15 mmol) to diethyl 2,5-diaminothiophene-3,4-dicarboxylate (48 mg, 0.19 mmol) followed by refluxing in isopropanol for 12 hours with a catalytic amount of TFA. The intermediate product was isolated as a yellow powder 3 (50 mg, 1.1 mmol 74%) after purification by flash chromatography. To the resulting product was added 2-thiophene carboxaldehyde (13 mg, 1.2 mmol) in isopropanol with a catalytic amount of TFA. The reaction was refluxed for 12 hours. The title product was isolated as a red colored powder following flash chromatography (37.5 mg, 0.1 mmol, 46%). 1H-NMR (400 MHz, [D] acetone): δ=8.75 (s, 1H), 8.69 (d, 1H, 3J=3.6), 7.86 (d, 1H, 3J=4.96), 7.78 (d, 1H, 3J=2.84), 7.71 (d, 1H, 3J=3.88), 7.59 (dd, 1H, 3J=5.04, 4J=0.76), 7.51 (d, 1H, 3J=3.68), 7.26 (dd, 1H, 3J=3.76, 4J=1.2), 7.17 (dd, 1H, 3J=3.68, 4J=1.36), 4.35 (m, 4H), 1.40 (m, 6H).
Workup
- customThis compound can be synthesized either step-wise
Sources & evidence
- ORD record
- ord-31f786d720004789a38e09667f3eaef5
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08034895B2
Reaction notes
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