1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(4-methyl-piperazin-1-yl)-2-piperidin-1-yl-phenyl]-amide

HRID 646900Notes

Reaction equation

HRID 646900 reaction equation
[K+].[C:2]([C:4]1[N:5]=[C:6]([C:17]([O-:19])=O)[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)#[N:3].[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33]C(C3OC(C#N)=CC=3)=O)=[C:29]([N:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[CH:28]=2)[CH2:23][CH2:22]1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:20][N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:17]([C:6]3[N:7]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[CH:8]=[C:4]([C:2]#[N:3])[N:5]=3)=[O:19])=[C:29]([N:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[CH:28]=2)[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 115028715-Cyano-N-[4-(4-Methylpiperazin-1-Yl)-2-Piperidin-1-Ylphenyl]furan-2-CarboxamideHCID 67188357potassium 4-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylate

Product 1

HCID 709034694-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(4-methyl-piperazin-1-yl)-2-piperidin-1-yl-phenyl]-amideYield 57.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A flask was charged with 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (0.043 g, 0.14 mmol) (as prepared in Example 3, step (d)), 4-(4-methyl-piperazin-1-yl)-2-piperidin-1-yl-phenylamine (0.028 g, 0.10 mmol) (as prepared in Example 5, step (b)), EDCI (0.030 g, 0.16 mmol), DMAP (0.012 g, 0.010 mmol), and DMF (0.5 mL) and was stirred for 12 h at RT and then 1 h at 60° C. The reaction mixture was loaded on a 10-g SPE cartridge (silica) and eluted with 10% MeOH/DCM to give 0.030 g (57%) of title compound. Mass spectrum (ESI, m/z): Calcd. for C27H41N7O2Si, 524.3 (M+H), found 524.1.

Workup

  1. custom1 h
  2. customat 60° C
  3. washeluted with 10% MeOH/DCM

Sources & evidence

ORD record
ord-dcaf9755fa6645f4bc0b4d09c1a5d9c9
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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