Pinonic acid → 2-[2-[3-(Carboxymethyl)-2,2-dimethyl-cyclobutyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788499Notes

Reaction equation

HRID 1788499 reaction equation
BrC1C=CC(O)=C([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)C=1.C([CH:40]1[CH2:43][CH:42]([CH2:44][C:45]([OH:47])=[O:46])[C:41]1([CH3:49])[CH3:48])(=O)C.[OH-].[K+]>C(O)C>[C:45]([CH2:44][CH:42]1[CH2:43][CH:40]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]4[N:22]([CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]5)[C:21]5[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=5[N:19]=4)[CH:14]=3)[N:9]=2)[C:41]1([CH3:49])[CH3:48])([OH:47])=[O:46]

Participants

5

Reactant 3

HCID 10130Pinonic acidHCID 14797Potassium HydroxideHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52761212-[2-[3-(Carboxymethyl)-2,2-dimethyl-cyclobutyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Following the procedure and workup for Compound 354, Compound 354e 100 mg, 0.256 mmol) was reacted with (3-acetyl-2,2-dimethyl-cyclobutyl)-acetic acid (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (21 mg, 16% yield). MS: 512.31 (M+H+); HPLC Procedure A, retention time=9.07 min.

Sources & evidence

ORD record
ord-e80f58ddc4ce449f857fd2bc8077933f
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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