1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67197065, compound

HRID 550800Notes

Reaction equation

HRID 550800 reaction equation
[CH:1]1([C:6]2[N:7]=[C:8]([N:17]3[CH2:22][CH2:21][CH:20]([CH2:23][C:24](O)=[O:25])[CH2:19][CH2:18]3)[C:9]3[CH2:14][S:13](=[O:16])(=[O:15])[CH2:12][C:10]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[NH4+].[NH4+].C1C=CC2N(O)N=[N:39]C=2C=1.CCN=C=NCCCN(C)C.[ClH:54].O1CCOCC1>C1COCC1.CN(C=O)C>[ClH:54].[CH:1]1([C:6]2[N:7]=[C:8]([N:17]3[CH2:18][CH2:19][CH:20]([CH2:23][C:24]([NH2:39])=[O:25])[CH2:21][CH2:22]3)[C:9]3[CH2:14][S:13](=[O:15])(=[O:16])[CH2:12][C:10]=3[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 517111Ammonium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 67197603HCID 67197603, compound

Product 1

HCID 67197065HCID 67197065, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 246 mg of [1-(2-cyclopentyl-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperidin-4-yl]acetic acid, 75 mg of ammonium carbonate, 0.11 g of HOBt, 0.16 g of EDCI, and 6 ml of DMF was stirred at ambient temperature for 3 days. The solvent was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with EtOAc. The organic phase obtained was washed with a saturated aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica-gel column chromatography (chloroform-MeOH) to yield a foamy product. This product was dissolved in THF, here was added 4M HCl-dioxane solution, the solution was concentrated under reduced pressure, the residue was washed with ether to yield 184 mg of [1-(2-cyclopentyl-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperidin-4-yl]acetamide hydrochloride.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic phase obtained
  5. washwas washed with a saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica-gel column chromatography (chloroform-MeOH)
  10. customto yield a foamy product
  11. concentrationthe solution was concentrated under reduced pressure
  12. washthe residue was washed with ether

Sources & evidence

ORD record
ord-8d26ce485d144b648a6d59625133c2e7
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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