1-(4-Cyanobenzyl)imidazole-5-carboxylic acid → 4-{5-[4-Hydroxymethyl-4-(2-methylbenzyl)piperidine-1-carbonyl]imidazol-1-ylmethyl}benzonitrile

HRID 1068436Notes

Reaction equation

HRID 1068436 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].Cl.CC1C=C(C=CC=1)CC1(CO)CCNCC1.Cl.[CH3:36][C:37]1[CH:51]=[CH:50][CH:49]=[CH:48][C:38]=1[CH2:39][C:40]1([CH2:46][OH:47])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>>[OH:47][CH2:46][C:40]1([CH2:39][C:38]2[CH:48]=[CH:49][CH:50]=[CH:51][C:37]=2[CH3:36])[CH2:45][CH2:44][N:43]([C:13]([C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:17][CH:16]=3)[CH:9]=[N:10][CH:11]=2)=[O:15])[CH2:42][CH2:41]1

Participants

4

Reactant 3

HCID 158851851-(4-Cyanobenzyl)imidazole-5-carboxylic acidHCID 211934014-(3-Methylbenzyl)-4-hydroxymethylpiperidine hydrochloride saltHCID 211934534-(2-Methylbenzyl)-4-hydroxymethylpiperidine hydrochloride salt

Product 1

HCID 211933694-{5-[4-Hydroxymethyl-4-(2-methylbenzyl)piperidine-1-carbonyl]imidazol-1-ylmethyl}benzonitrile

Procedure

The title compound was prepared as white solid according to the procedure described in Example 38, Step A-B substituting 1-(4-cyanobenzyl)imidazole-5-acetic acid-lithium chloride with 1-(4-cyanobenzyl)imidazole-5-carboxylic acid and 4-(3-methylbenzyl)-4-hydroxymethylpiperidine hydrochloride salt with 4-(2-methylbenzyl)-4-hydroxymethylpiperidine hydrochloride salt (Example 35) in Step B. The crude product was purified with column chromatography on silica gel eluting with 2-5% methanol in chloroform.

Workup

  1. customThe crude product was purified with column chromatography on silica gel eluting with 2-5% methanol in chloroform

Sources & evidence

ORD record
ord-737498b48903489293def24793d23dfb
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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