Dicyclohexylcarbodiimide → HCID 10073128, compound

HRID 1374734Notes

Reaction equation

HRID 1374734 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([C:16]([OH:18])=O)[CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:21].[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:25]=1.C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1>CN(C=O)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([C:16]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:25]=3)=[O:18])[CH:11]=2)=[O:9])=[CH:4][C:3]=1[CH3:21]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11535728Ethyl [4-(aminomethyl)phenyl]acetateHCID 11694935HCID 11694935, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 10073128HCID 10073128, compoundYield 127.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.3 g (4.5 mmol) of 6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidine-4-carboxylic acid and 1.042 g (5.4 mmol) of ethyl (4-aminomethylphenyl)acetate were dissolved in 30 ml of DMF, after which 1.02 g (4.9 mmol) of dicyclohexylcarbodiimide and 0.607 g (4.5 mmol) of hydroxybenzotriazole were added at 5° C. The mixture was stirred for 5 hours (h) and filtered with suction. The solvent was removed in vacuo and the residue was taken up in ethyl acetate; this solution was washed with a saturated aqueous solution of NaHCO3. The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. This resulted in 2.66 g of product, which was further purified by means of preparative HPLC. MS (ES+): m/e=464.19.

Workup

  1. filtrationfiltered with suction
  2. customThe solvent was removed in vacuo
  3. washthis solution was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f9a7466427a940a7a89af05fd0736dc2
Source dataset
uspto-grants-2007_01
Patent number
US07166609B2

Reaction notes

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