Potassium Hydroxide → 2-[2-(3-Carbamoyl-4-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788492Notes

Reaction equation

HRID 1788492 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([C:40]1[CH:41]=[CH:42][C:43]([OH:49])=[C:44]([CH:48]=1)[C:45]([NH2:47])=[O:46])(=O)C.[OH-].[K+]>C(O)C>[C:45]([C:44]1[CH:48]=[C: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[CH2:28][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)[CH:41]=[CH:42][C:43]=1[OH:49])(=[O:46])[NH2:47]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1982125-AcetylsalicylamideHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52759992-[2-(3-Carbamoyl-4-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidYield 10%

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 5-acetyl-2-hydroxy-benzamide (0.256 mmol) in ethanol (2 mL) using 10% w/v KOH in Ethanol (506 μL, 0.64 mmol) to produce the title compound (13 mg, 10% yield). MS: 507.24 (M+H+); HPLC Procedure A, retention time=10.36 min.

Sources & evidence

ORD record
ord-d8474d7d175943d79dbc7974c9e6d8b8
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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