Triethylamine → HCID 59352085, compound

HRID 1407899Notes

Reaction equation

HRID 1407899 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[O:27][C:26]([C:28]([OH:30])=O)=[CH:25][CH:24]=1.S(Cl)(Cl)=O.Cl.[CH3:36][NH:37][CH3:38].C(N(CC)CC)C>CN(C)C=O.C(Cl)(Cl)Cl.ClCCl>[CH3:36][N:37]([CH3:38])[C:28]([C:26]1[O:27][C:23]([CH2:22][N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]3([CH2:14][O:13][C:12]4[CH:15]=[C:16]5[C:20](=[CH:21][C:11]3=4)[CH2:19][CH2:18][O:17]5)[C:2]2=[O:1])=[CH:24][CH:25]=1)=[O:30]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 24386Thionyl ChlorideHCID 59352422HCID 59352422, compound

Product 1

HCID 59352085HCID 59352085, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3-indol]-1′(2′H)-yl)methyl]furan-2-carboxylic acid (4.85 g, 12 mmol), thionyl chloride (11.90 g, 100 mmol) and a few drops of N,N-dimethylformamide in chloroform (60 mL) was stirred at ambient temperature for 16 h. The solvent and excess of thionyl chloride were evaporated under reduced pressure. The residue was dissolved in dichloromethane (50 mL). To the above solution (5 mL, 1.2 mmol) was added dimethylamine hydrochloride (0.81 g, 10 mmol), and triethylamine (1.01 g, 10 mmol). The mixture was stirred at ambient temperature for 3 h. The reaction mixture was diluted with dichloromethane (100 mL) and extracted with water (2×100 mL), dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography with dichloromethane-methanol (100:1-20:1) to afford N,N-dimethyl-5-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]furan-2-carboxamide (0.22 g, 42%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.31-6.90 (m, 5H), 6.43-6.37 (m, 3H), 4.97 (ABq, 2H), 4.78 (ABq, 2H), 4.52 (t, J=8.6 Hz, 2H), 3.11 (s, 6H), 2.96 (t, J=8.6 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 177.2, 161.6, 161.0, 159.4, 151.3, 147.5, 142.2, 132.6, 129.1, 124.1, 123.7, 121.0, 120.4, 119.5, 116.8, 110.4, 109.8, 92.9, 80.1, 72.6, 57.4, 37.1, 28.8; MS (ES+) m/z 431.1 (M+1).

Workup

  1. customThe solvent and excess of thionyl chloride were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. stirringThe mixture was stirred at ambient temperature for 3 h
  4. extractionextracted with water (2×100 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography with dichloromethane-methanol (100:1-20:1)

Sources & evidence

ORD record
ord-9a3646bacd0c46f08b3ef4a88415808f
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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