Triethylamine → HCID 59352085, compound

HRID 1965763Notes

Reaction equation

HRID 1965763 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) δ177.2, 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-7f1212352e1d4efba8a48c0d559dfe27
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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