Triethylamine → HCID 73442650, compound

HRID 530684Notes

Reaction equation

HRID 530684 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][S:9][C:8]=2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:20]12[C:28](=[O:29])[O:27][C:25](=[O:26])[C:21]=1[CH2:22][CH2:23][CH2:24]2>C1COCC1>[C:1]1([C:7]2[CH:11]=[CH:10][S:9][C:8]=2[NH:12][C:28]([C:20]2[CH2:24][CH2:23][CH2:22][C:21]=2[C:25]([OH:27])=[O:26])=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 234643023-Phenyl-2-thiophenamine

Product 1

HCID 73442650HCID 73442650, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Phenyl-thiophen-2-ylamine (73 mg, 417 μmol, Int1.1), NEt3 (84.3 mg, 116 μL, 833 μmol) and 1-cyclopentene-1,2-dicarboxylic anhydride (144 mg, 1.04 mmol) were dissolved in dry THF (3 mL). The green-yellow suspension was stirred at RT over the week-end and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC (MeOH/H2O with 0.1% formic acid) to give the title compound as a yellow oil (47 mg, 32%, purity estimated at 90%). MS (ESI): m/z=312.2 [M−H]−.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by preparative HPLC (MeOH/H2O with 0.1% formic acid)

Sources & evidence

ORD record
ord-f3305fdac30b41afa7ceca56cf863722
Source dataset
uspto-grants-2016_05
Patent number
US09353102B2

Reaction notes

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