Potassium Hydroxide → 2-[2-[2-(4-Chlorophenyl)-4-methyl-thiazol-5-yl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788511Notes

Reaction equation

HRID 1788511 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:43]=[CH:42][C:41]([C:44]2[S:45][C:46](C(=O)C)=[C:47]([CH3:49])[N:48]=2)=[CH:40][CH:39]=1.[OH-].[K+]>C(O)C>[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([C:44]2[S:45][C:46]([C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:18]5[N:22]([CH:23]6[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]6)[C:21]6[CH:29]=[CH:30][C:31]([C:33]([OH:35])=[O:34])=[CH:32][C:20]=6[N:19]=5)[CH:14]=4)[N:9]=3)=[C:47]([CH3:49])[N:48]=2)=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27284591-(2-(4-Chlorophenyl)-4-methyl-1,3-thiazol-5-yl)ethan-1-oneHCID 52759802-[2-(5-Bromo-2-hydroxy-phenyl)-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

Product 1

HCID 52760362-[2-[2-(4-Chlorophenyl)-4-methyl-thiazol-5-yl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidYield 19%

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-(4-chloro-phenyl)-4-methyl-thiazol-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 (27 mg, 19% yield). MS: 580.19 (M+H+); HPLC Procedure B, retention time=9.18 min.

Sources & evidence

ORD record
ord-e6b83a0383664f9789a0c05c0c33737e
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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