2'-Nitroacetophenone → HCID 178524148, compound

HRID 1788495Notes

Reaction equation

HRID 1788495 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](C5CCCCC5)[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.[N+:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1C(=O)C)([O-])=[O:38].[OH-:49].[K+]>C(O)C>[N+:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:13]1([C:18]2[NH:22][C:21]3[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=3[N:19]=2)[CH:12]=[CH:11][C:10]2[N:9]=[CH:8][CH:17]=[CH:16][C:15]=2[CH2:14]1)([O-:38])=[O:49]

Participants

5

Reactant 3

HCID 113462'-NitroacetophenoneHCID 14797Potassium HydroxideHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 178524148HCID 178524148, 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-(2-nitro-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 (11 mg, 10% yield). MS: 493.21 (M+H+); HPLC Procedure A, retention time=12.72 min.

Sources & evidence

ORD record
ord-f5c7f22729a94281b64769d245a1673a
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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