Potassium Carbonate → (E)-3-[2-n-Butyl-1-{(4-cyanophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

HRID 36999Notes

Reaction equation

HRID 36999 reaction equation
C(C1[NH:6]C(C=O)=C(CC2C=CC(C#N)=CC=2)N=1)CCC.[CH2:21]([C:25]1[N:26]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39](OCC)=O)=[CH:35][C:34]=2Cl)[C:27]([CH:30]=O)=[CH:28][N:29]=1)[CH2:22][CH2:23][CH3:24].[S:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[CH2:50][CH2:51][C:52]([O:54]C)=[O:53].C(C1N(CC2C=CC=CC=2Cl)C(/C(/C)=C(\C2C=CN=CC=2)/C(O)=O)=CN=1)CCC.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>>[CH2:21]([C:25]1[N:26]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]#[N:6])=[CH:37][CH:38]=2)[C:27](/[CH:30]=[C:51](\[CH2:50][C:46]2[S:45][CH:49]=[CH:48][CH:47]=2)/[C:52]([OH:54])=[O:53])=[CH:28][N:29]=1)[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 6

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 566367Methyl 3-(thiophen-2-yl)propanoateHCID 199367892-n-Butyl-1-(4-carboethoxy-2-chlorobenzyl)imidazole-5-aldehydeHCID 86746549(E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(4-pyridyl)-methyl-2-propenoic acidHCID 178441598HCID 178441598, compound

Product 1

HCID 14952919(E)-3-[2-n-Butyl-1-{(4-cyanophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

Procedure

The title compound was prepared using 2-n-butyl-[(4cyanophenyl)methyl]imidazole-5-aldehyde (prepared by the method of Example 42 describing the preparation of 2-n-butyl-1-[(4-carboethoxy-2-chlorophenyl)methyl]imidazole-5-aldehyde) and methyl 3-(2-thienyl)propanoate by the procedure of Example 1 (iv, Method B), except, instead of basic hydrolysis of the ester with sodium hydroxide, potassium carbonate hydrolysis was employed; mp 190°-192° C.

Workup

  1. customprepared by the method of Example 42 describing

Sources & evidence

ORD record
ord-daa1f6b5924e47dc938066ff6db2a6b1
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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