p-Aminoacetophenone → HCID 5275984, compound

HRID 1788491Notes

Reaction equation

HRID 1788491 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([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:7]=1.[NH2:37]C1C=CC(C(=O)C)=CC=1.[OH-].[K+]>C(O)C>[NH2:37][C:3]1[CH:2]=[CH:7][C:6]([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:5][CH:4]=1

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 14797Potassium HydroxideHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 5275984HCID 5275984, 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-amino-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 (14 mg, 10% yield). MS: 463.23 (M+H+); HPLC Procedure A, retention time=8.62 min.

Sources & evidence

ORD record
ord-172f2be876094ff0ae6346fa773a22d3
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

Loading…