1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester

HRID 2190652Notes

Reaction equation

HRID 2190652 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][O:27][C:28]([C@H:30]1[CH2:35][CH2:34][C@H:33]([C:36](O)=[O:37])[CH2:32][CH2:31]1)=[O:29].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:26][O:27][C:28]([CH:30]1[CH2:35][CH2:34][CH:33]([C:36]([N:22]2[CH2:23][CH2:24][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:12](=[O:25])[NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=4)=[CH:14][N:15]=3)[CH2:20][CH2:21]2)=[O:37])[CH2:32][CH2:31]1)=[O:29]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59318114N-(3-tert-Butyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 178501163HCID 178501163, compound

Product 1

HCID 593180854-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(3-tert-butyl-phenyl)-6-piperazin-1-yl-nicotinamide (100 mg, 0.29 mmol) in CH2Cl2 (10 mL) was treated with trans-1,4-cyclohexane dicarboxylic acid monomethyl ester. (110 mg, 0.59 mmol) and EDCI (230 mg, 1.18 mmol) at room temperature. After stirring overnight the reaction mixture was partitioned between EtOAc and water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on a silica gel column with 20-100% EtOAc in hexanes gradient to afford the product (120 mg, Yield: 80%). HRMS m/z calcd for C29H38N4O4 [M+H]+: 507.2966. Found: 507.2968.

Workup

  1. customat room temperature
  2. customwas partitioned between EtOAc and water
  3. customThe organic layer was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column with 20-100% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-ff662d925520437888b5f5d7d5ff91d5
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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