Potassium Hydroxide → HCID 5276081, compound

HRID 1788496Notes

Reaction equation

HRID 1788496 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.[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C:51](=O)[CH3:52])=[C:47]([OH:54])[C:46]=1[CH3:55])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[OH-].[K+]>C(O)C>[CH2:37]([O:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:52]=[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:47]([OH:54])[C:46]=1[CH3:55])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 7361854'-Benzyloxy-2'-hydroxy-3'-methylacetophenoneHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 5276081HCID 5276081, compoundYield 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 1-(4-benzyloxy-2-hydroxy-3-methyl-phenyl)-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 (73 mg, 10% yield). MS: 584.29 (M+H+); HPLC Procedure A, retention time=18.27 min.

Sources & evidence

ORD record
ord-51db0a9a57474c7c8a17668faefa5361
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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