Citric Acid → HCID 21876503, compound

HRID 858444Notes

Reaction equation

HRID 858444 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:24][CH3:25])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3].[CH3:26][S:27](Cl)(=[O:29])=[O:28].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([NH:23][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:24][CH3:25])=[CH:12][CH:13]=1)(=[O:4])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21875779HCID 21875779, compound

Product 1

HCID 21876503HCID 21876503, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-[4-(5-amino-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl propionate (step 4, 1.18 g, 3.50 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (0.40 mL, 5.25 mmol) and pyridine (0.42 mL, 5.25 mmol) at room temperature. After stirring for 6 h, the mixture was poured into 10% aqueous citric acid (100 mL) and extracted with ethyl acetate (100 mL). The aqueous layer was made basic with saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL). The combined organic extracts were washed with brine (100 mL) and dried (MgSO4), and concentrated to afford 1.28 g (88%) of the title compound as brown amorphous: 1H-NMR (CDCl3) δ 8.47 (1H, s), 7.66 (1H, d, J=1.7 Hz), 7.50 (2H, d, J=8.4 Hz), 7.42 (1H, dd, J=2.0, 8.8 Hz), 7.41 (2H, d, J=8.4 Hz), 7.09 (1H, d, J=8.8 Hz), 4.39 (2H, t, J=7.0 Hz), 3.09 (2H, t, J=6.8 Hz), 3.00 (2H, q, J=7.7 Hz), 2.36 (2H, q, J=7.7 Hz), 1.42 (3H, t, J=7.7 Hz), 1.15 (3H, t, J=7.5 Hz).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic extracts were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-235598cee8c24eaeba39471fefcd7552
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

Loading…