4-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride → Ethyl 1-[3-(4-cyanobenzyl)-2-methyl-3H-imidazol-4-ylmethyl]-4-[3-(methanesulfonylaminomethyl)-benzyl]piperidine-4-carboxylate

HRID 1068449Notes

Reaction equation

HRID 1068449 reaction equation
Cl.[CH3:2][S:3]([NH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][C:12]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:5])=[O:4].Cl.C(C1C=CC(CN2C(CCl)=CN=C2)=CC=1)#N.Cl.[C:44]([C:46]1[CH:60]=[CH:59][C:49]([CH2:50][N:51]2[C:55]([CH2:56]Cl)=[CH:54][N:53]=[C:52]2[CH3:58])=[CH:48][CH:47]=1)#[N:45]>>[C:44]([C:46]1[CH:47]=[CH:48][C:49]([CH2:50][N:51]2[C:55]([CH2:56][N:15]3[CH2:16][CH2:17][C:12]([CH2:11][C:10]4[CH:23]=[CH:24][CH:25]=[C:8]([CH2:7][NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH:9]=4)([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14]3)=[CH:54][N:53]=[C:52]2[CH3:58])=[CH:59][CH:60]=1)#[N:45]

Participants

4

Reactant 3

HCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 21193259Ethyl 4-[3-(methanesulfonylamino-methyl)benzyl]piperidine-4-carboxylate hydrochloride saltHCID 211933481-(4-Cyanobenzyl)-5-chloromethyl-2-methylimidazole hydrochloride salt

Product 1

HCID 21193334Ethyl 1-[3-(4-cyanobenzyl)-2-methyl-3H-imidazol-4-ylmethyl]-4-[3-(methanesulfonylaminomethyl)-benzyl]piperidine-4-carboxylate

Procedure

The title compound was prepared using the protocol described in Example 61, Step C substituting methyl 4-(3-methylbenzyl)piperidine-4-carboxylate hydrochloride salt with ethyl 4-[3-(methanesulfonylamino-methyl)benzyl]piperidine-4-carboxylate hydrochloride salt, and 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt with 1-(4-cyanobenzyl)-5-chloromethyl-2-methylimidazole hydrochloride salt (Example 53, Step B). After column chromatography on silica gel, the free base obtained was triturated with anhydrous diethyl ether. The white solid precipitated was filtered, and residual solvent was removed under vacuum overnight to provide the title compound.

Workup

  1. customThe title compound was prepared
  2. customAfter column chromatography on silica gel, the free base obtained
  3. customwas triturated with anhydrous diethyl ether
  4. customThe white solid precipitated
  5. filtrationwas filtered
  6. customresidual solvent was removed under vacuum overnight

Sources & evidence

ORD record
ord-5bef9783cac04f11a92f75df1646f015
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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