2-Methoxyethanol → HCID 117601943, compound

HRID 1773740Notes

Reaction equation

HRID 1773740 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([C:15]([OH:48])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[C:16]2[C:24]3[N:23]=[C:22]([O:25]CC)[N:21](C(OC(C)(C)C)=O)[C:20]=3[CH:19]=[C:18]([C:35]3[C:36]([CH3:41])=[N:37][O:38][C:39]=3[CH3:40])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH3:41][C:36]1[C:35]([C:18]2[CH:17]=[C:16]([C:15]([OH:48])([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:14]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[C:24]3[NH:23][C:22](=[O:25])[NH:21][C:20]=3[CH:19]=2)=[C:39]([CH3:40])[O:38][N:37]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 117601854HCID 117601854, compound

Product 1

HCID 117601943HCID 117601943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-methoxyethanol (25 mg, 0.33 mmol) was dissolved in THF (0.5 mL) and cooled to 0° C. Sodium hydride (8 mg, 0.33 mmol) was added in one portion and the reaction was allowed to come to rt and stir for 10 minutes. The reaction was then cooled back to 0° C. and tert-butyl 4-((6-chloropyridin-2-yl)(hydroxy)(pyridin-2-yl)methyl)-6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazole-1-carboxylate (24 mg, 0.04 mmol) was added and the reaction was sealed and heated to 80° C. overnight. Reaction was concentrated and the residue was taken up in EtOH (1.5 mL) and 4M HCl/dioxane (0.5 mL) and heated for 2 hours at 60° C. The reaction was cooled to rt and filtered to remove the sodium salt. Filterate was concentrated to afford the desired product as a brown film.

Workup

  1. customto come to rt
  2. temperatureThe reaction was then cooled back to 0° C.
  3. customthe reaction was sealed
  4. temperatureheated to 80° C. overnight
  5. customReaction
  6. concentrationwas concentrated
  7. temperature4M HCl/dioxane (0.5 mL) and heated for 2 hours at 60° C
  8. temperatureThe reaction was cooled to rt
  9. filtrationfiltered
  10. customto remove the sodium salt
  11. concentrationFilterate was concentrated

Sources & evidence

ORD record
ord-a5025dcfebf9455aae88724182113461
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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