Ethyl orthoformate → 3-(2-Pyrrolidin-1-yl-ethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

HRID 69141Notes

Reaction equation

HRID 69141 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:5]=1.[CH2:20](OC(OCC)OCC)C>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[CH:20][N:11]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[C:6]=2[CH:5]=1)=[O:19]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 57917314HCID 57917314, compound

Product 1

HCID 579172413-(2-Pyrrolidin-1-yl-ethyl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Procedure

4-Amino-3-(2-pyrrolidin-1-yl-ethylamino)-benzoic acid methyl ester (xii) (1.14 g, 4.33 mmol) and triethylorthoformate (20 mL, 120 mmol) were heated at 120° C. for 18 h before being evaporated to dryness. The residue was taken in EtOAc and aqueous saturated NaHCO3. The aqueous layer was extracted 2 times with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to afford the title compound as a brown oil (tR 1.83 min (conditions 8), MH+=274).

Workup

  1. custombefore being evaporated to dryness
  2. extractionThe aqueous layer was extracted 2 times with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-309dde2ac1664ddf9a793a3e8fb8275d
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…