1,2-Dimethoxyethane → HCID 70090434, compound

HRID 703785Notes

Reaction equation

HRID 703785 reaction equation
[H-].[Na+].[C:3]1(=[O:16])[C:8]2[C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:7]=2[CH2:6][CH2:5][NH:4]1.Cl[CH2:18][C:19]1[N:20]=[CH:21][N:22](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:23]=1[CH3:24].[C:44](=[O:47])([OH:46])[O-].[Na+].C(COC)[O:50]C>O.C(O)(=O)C>[C:10]([OH:50])(=[O:11])/[CH:9]=[CH:15]\[C:44]([OH:46])=[O:47].[CH3:24][C:23]1[NH:22][CH:21]=[N:20][C:19]=1[CH2:18][N:4]1[CH2:5][CH2:6][C:7]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[C:3]1=[O:16]

Participants

8

Reactant 5

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 110469654-(Chloromethyl)-5-methyl-1-trityl-1H-imidazoleHCID 20074904HCID 20074904, compound

Product 1

HCID 70090434HCID 70090434, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium hydride (73% dispersion in oil; 20 mg) was added to a stirred solution of 3,4-dihydrobenzofuro[3,2-c]pyridin-1(2H)-one (95 mg) in dry dimethoxyethane (3 ml) under nitrogen. After 30 min. 4-(chloromethyl)-5-methyl-1-(triphenylmethyl)-1H-imidazole (227 mg) was added and the mixture was stirred at 50° for 18h. Acetic acid (1 ml) and water (1 ml) were added and the solution was heated at reflux for 1h. The mixture was poured into 8% sodium bicarbonate solution (30 ml) and extracted with dichloromethane (3×15 ml). The combined, dried organic extracts were evaporated to give a solid (ca.420 mg) which was purified by SPCC eluting with System A (200:10:1) to give the free base of the title compound (77 mg). This was dissolved in absolute ethanol (2 ml) and treated with a solution of maleic acid (33 mg) in absolute ethanol (1 ml). The solvent was removed in vacuo and the residue was triturated with dry ether (3×5 ml) to give the title compound (85mg), m.p. 285°-286°, t.l.c. (System A, 200:10:1) Rf 0.24.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 1h
  3. extractionextracted with dichloromethane (3×15 ml)
  4. customdried organic extracts were evaporated
  5. customto give a solid (ca.420 mg) which
  6. customwas purified by SPCC
  7. washeluting with System A (200:10:1)

Sources & evidence

ORD record
ord-027323f5828b48a6ba8eba935ed23525
Source dataset
uspto-grants-1991_01
Patent number
US04985422

Reaction notes

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