Dimethylformamide → HCID 59497300, compound

HRID 1747289Notes

Reaction equation

HRID 1747289 reaction equation
C(O[C:4](=[O:28])/[CH:5]=[CH:6]/[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:8]1=[O:27])C.[O:29]([CH3:31])[Na].CN(C=[O:36])C>>[CH3:31][O:29][CH:6]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[C:8]1=[O:27])[CH2:5][C:4]([OH:28])=[O:36]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 59497305HCID 59497305, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 59497300HCID 59497300, compound

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-3-(3-Naphthalen-1-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-acrylic acid ethyl ester (0.1 g, 0.27 mmol) in DMF (1 mL) was added NaOCH3 (1.1 mL, 0.5 M in MeOH). The reaction mixture was stirred at 60° C. for 2 h (due to poor solubility, the reaction was heated). The reaction mixture was concentrated. The reaction mixture was diluted with 1N HCl and then extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. Since LCMS indicated that there was a small amount of the product in methyl ester form, the resulting residue was diluted with methanol and treated with 2N NaOH for 30 min. The mixture was acidified by adding 1N HCl and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 39 mg of the title compound as an off-white solid. LCMS (ESMS): m/z 377.31 (M+H+).

Workup

  1. temperaturethe reaction was heated)
  2. concentrationThe reaction mixture was concentrated
  3. additionThe reaction mixture was diluted with 1N HCl
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. additionthe resulting residue was diluted with methanol
  8. additiontreated with 2N NaOH for 30 min
  9. additionby adding 1N HCl
  10. extractionextracted with CH2Cl2
  11. dry with materialThe organic phase was dried over Na2SO4
  12. concentrationconcentrated
  13. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-f84dae4449ee479fae92b374db968d2b
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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