Triethylamine → HCID 69519963, compound

HRID 1831317Notes

Reaction equation

HRID 1831317 reaction equation
[OH:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]2=[O:17])=[CH:4][CH:3]=1.C(NC1C=CC([O:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([O:42][Si](C(C)(C)C)(C)C)[CH2:38][CH2:37]2)=O)=NC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C=O.Cl>[CH3:16][C:11]1([CH3:15])[CH2:12][C:13](=[O:14])[N:8]([C:5]2[CH:6]=[N:7][C:2]([O:1][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]3)=[O:33])=[CH:3][CH:4]=2)[C:9](=[O:17])[CH2:10]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterHCID 178426979HCID 178426979, compound

Product 1

HCID 69519963HCID 69519963, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6′-hydroxy-4,4-dimethyl-4,5-dihydro-3H-[1,3′]bipyridinyl-2,6-dione (468 mg, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, filtered over a short pad of silicagel and washed with ethyl acetate. The solvent was evaporated in vacuo and the residue was dissolved in 1N HCl in ethyl acetate (10 mL, 10.0 mmol). After stirring for 1.5 hours at room temperature the solvent was evaporated in vacuo. The white solid was washed with a small amount of ethyl acetate and diethyl ether and dissolved in a few millilitres of dichloromethane and triethylamine (1 mL). Purification by flash column chromatography (SiO2, ethyl acetate:acetone 90:10) yielded the title compound (182 mg, 25% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. filtrationfiltered over a short pad of silicagel
  4. washwashed with ethyl acetate
  5. customThe solvent was evaporated in vacuo
  6. customwas evaporated in vacuo
  7. washThe white solid was washed with a small amount of ethyl acetate and diethyl ether
  8. dissolutiondissolved in a few millilitres of dichloromethane
  9. customPurification by flash column chromatography (SiO2, ethyl acetate:acetone 90:10)

Sources & evidence

ORD record
ord-5e74d0b34c5648609bb5f82f0a4dbb8f
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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