Potassium Hydroxide → 1-Cyclohexyl-2-[2-(7-hydroxybenzofuran-2-yl)-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788482Notes

Reaction equation

HRID 1788482 reaction equation
BrC1C=CC(O)=C(C2C=[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.[OH:37][C:38]1[C:46]2[O:45][C:44]([C:47](=O)[CH3:48])=[CH:43][C:42]=2[CH:41]=[CH:40][CH:39]=1.[OH-].[K+]>C(O)C>[CH:23]1([N:22]2[C:21]3[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=3[N:19]=[C:18]2[C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:47]([C:44]2[O:45][C:46]4[C:38]([OH:37])=[CH:39][CH:40]=[CH:41][C:42]=4[CH:43]=2)[CH:48]=[CH:16]3)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 5953292-Acetyl-7-hydroxybenzofuranHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52760311-Cyclohexyl-2-[2-(7-hydroxybenzofuran-2-yl)-6-quinolyl]benzimidazole-5-carboxylic acidYield 20%

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 1-(7-hydroxy-benzofuran-2-yl)-ethanone (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in ethanol (506 μL, 0.64 mmol) to produce the title compound (19 mg, 20% yield). MS: 504.22 (M+H+); HPLC Procedure A, retention time=12.20 min.

Sources & evidence

ORD record
ord-2cb1bd4899fc45fe94e854b6f97a9f52
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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