Potassium Hydroxide → 1-Cyclohexyl-2-[2-[3-(3,4-dichlorophenyl)isoxazol-5-yl]-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788507Notes

Reaction equation

HRID 1788507 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.[Cl:37][C:38]1[CH:39]=[C:40]([C:45]2[CH:49]=[C:48](C(=O)C)[O:47][N:46]=2)[CH:41]=[CH:42][C:43]=1[Cl:44].[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:8]([C:48]2[O:47][N:46]=[C:45]([C:40]4[CH:41]=[CH:42][C:43]([Cl:44])=[C:38]([Cl:37])[CH:39]=4)[CH:49]=2)[CH:17]=[CH:16]3)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27455581-[3-(3,4-Dichlorophenyl)Isoxazol-5-Yl]Ethan-1-OneHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52760981-Cyclohexyl-2-[2-[3-(3,4-dichlorophenyl)isoxazol-5-yl]-6-quinolyl]benzimidazole-5-carboxylic acidYield 15%

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-[3-(3,4-dichloro-phenyl)-isoxazol-5-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 (21 mg, 15% yield). MS: 583.16 (M+H+); HPLC Procedure B, retention time=8.77 min.

Sources & evidence

ORD record
ord-670b118e4ab741148e6a2752f946a6b4
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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