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

HRID 2190660

Reaction equation

HRID 2190660 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:23])[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[C@H:24]1([C:33](O)=[O:34])[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1.CCN=C=NCCCN(C)C>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:33]([CH:24]4[CH2:25][CH2:26][CH:27]([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]4)=[O:34])[CH2:21][CH2:22]3)=[N:13][CH:12]=2)=[O:23])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59318071N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 178525731HCID 178525731, compound

Product 1

HCID 593179934-{4-[5-(3-Iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acidYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide (60 mg, 0.14 mmol), trans-1,4-cyclohexane dicarboxylic acid (122 mg, 0.71 mmol) in DMF (10 mL) was treated with EDCI (130 mg, 0.71 mmol). After stirring overnight the reaction mixture was partitioned between EtOAc and water. The water layer was made basic to pH 13 with solid NaOH. The EtOAc layer was removed and then the water layer was acidified to pH 5 with aq conc. HCl and extracted again with EtOAc. The EtOAc layer obtained after the latter extraction was dried over Na2SO4, filtered and concentrated to the product (10 mg, Yield: 12%). HRMS m/z calcd for C25H29N4O4I [M+H]+: 577.1306. Found: 577.1306.

Workup

  1. customwas partitioned between EtOAc and water
  2. customThe EtOAc layer was removed
  3. extractionextracted again with EtOAc
  4. customThe EtOAc layer obtained
  5. extractionafter the latter extraction
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7c51d01c96c04fc09b91fada97e578aa
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Linked notes

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