Ebastine → Terfenadine

HRID 1504588Notes

Reaction equation

HRID 1504588 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19](OC(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:18][CH2:17]2)=[O:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3].CC(C(O)=O)(C1C=CC(C(CCCN2CCC([O:56][CH:57]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)CC2)=O)=CC=1)C>CS(C)=O>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:12])[CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:57]([OH:56])([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:18][CH2:17]2)=[CH:9][CH:10]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 3191Ebastine2×HCID 65820Carebastine2×

Product 1

HCID 5405Terfenadine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To prepare the 10 mM stock solution of PS1, 1 mg of PS1 having a molecular weight of 618.8 was added to 162 μl of DMSO. For preparing the 50 mM stock solution of ebastine, 10 mg of ebastine having a molecular weight of 469.66 was added to 426 μl of DMSO. In preparing the 25 mM solution of carebastine, 1 mg of carebastine having a molecular weight of 499.65 was added to 80μ of DMSO. To obtain the 50 mM terfenadine stock solution 1.5 mg of terfenadine having a molecular weight of 471.7 was added to 64 μl of ETOH. To prepare the 50 mM stock solution of fexofenadine, 10 mg of fexofenadine chloride having a molecular weight of 538.12 was added to 372 μl of DMSO. Further, to prepare the 50 mM stock solution of astemizole, 10 mg of astemizole having a molecular weight of 458.57 was added to 436 μl of DMSO. Table 10 then lists the preparation of the solutions for use in the tests above.

Workup

  1. customTo prepare the 10 mM stock solution of PS1, 1 mg of PS1

Sources & evidence

ORD record
ord-881efdbfabe34b81ad2ad5f50b9381ba
Source dataset
uspto-grants-2015_12
Patent number
US09216181B2

Reaction notes

Loading…