Pyridine → HCID 86587627, compound

HRID 1358588Notes

Reaction equation

HRID 1358588 reaction equation
Cl.[SH:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=3[N:17]=2)=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].N1C=CC=CC=1.[O:34]1CC[CH2:36][CH2:35]1.C(OC(=O)C)(=O)C>CN(C)C=O>[C:35]([S:2][CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[N:20]([CH3:21])[C:19]3[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:18]=3[N:17]=2)=[CH:12][CH:13]=1)[C:4]([OH:6])=[O:5])(=[O:34])[CH3:36]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 86590621HCID 86590621, compound

Product 1

HCID 86587627HCID 86587627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-mercapto-3-[4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)phenyl]propionic acid hydrochloride (1.5 g), pyridine (0.87 g), tetrahydrofuran (30 ml) and N,N-dimethylformamide (30 ml) was added acetic anhydride (0.56 g). The mixture was stirred at room temperature for 5 hours and allowed to stand for 36 hours and then concentrated. The residual insoluble material was collected by filtration and washed with ethyl acetate to afford the title compound (1.55 g, mp 209-214° C., pale yellow powder).

Workup

  1. waitto stand for 36 hours
  2. concentrationconcentrated
  3. filtrationThe residual insoluble material was collected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ef59ddc8c0a442608dbdacf376f5ca26
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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