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Triethylamine → HCID 69519963, compound

HRID 1179941
Notes
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Reaction equation

HRID 1179941 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 AcidSolvent
HCID 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 1 N 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 milliliters 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 milliliters of dichloromethane
  9. customPurification by flash column chromatography (SiO2, ethyl acetate:acetone 90:10)

Sources & evidence

ORD record
ord-d46895e166a64cc3bbe95a592ddef92a
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07279470B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes