Triethylamine → HCID 69923560, compound

HRID 2414407Notes

Reaction equation

HRID 2414407 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([O:13]CC)=O)=[C:5]([O:16][CH2:17][CH2:18][NH:19][C:20](=[O:41])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:23][CH:22]=2)[CH:4]=1)#[N:2].[OH-].[Na+].O[N:45]1C2C=CC=CC=2N=N1.C(=O)([O-])N.[NH4+].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>C(O)C.CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:45])=[O:13])=[C:5]([O:16][CH2:17][CH2:18][NH:19][C:20](=[O:41])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:23][CH:22]=2)[CH:4]=1)#[N:2]

Participants

10

Reactant 6

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 517232Ammonium CarbamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69921131HCID 69921131, compound

Product 1

HCID 69923560HCID 69923560, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g (5.33 mmol) of ethyl 3-[4-cyano-2-(2-(4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoylamino)ethoxy)phenyl]acrylate was dissolved in 100 ml of ethanol. 15 ml of 1 N aqueous sodium hydroxide solution was added to the obtained solution, and they were stirred at room temperature overnight. The solvent was evaporated under reduced pressure. 1 N aqueous hydrochloric acid/ice solution was added to the obtained crude product, and they were treated with ethyl acetate as the extraction solvent in an ordinary manner to obtain the crude product. 30 ml of N,N-dimethylformamide, 0.75 g (5.55 mmol) of 1-hydroxybenzotriazole (hydrous), 1.40 g (25.2 mmol) of ammonium carbamate, 2 ml (0.015 mmol) of triethylamine and 2.12 g (11.09 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to the crude product, and they were stirred overnight. After the evaporation of the solvent followed by the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. addition1 N aqueous hydrochloric acid/ice solution was added to the
  3. customobtained crude product, and they
  4. customto obtain the crude product
  5. stirringwere stirred overnight
  6. customAfter the evaporation of the solvent
  7. customthe solvent was evaporated
  8. customthe obtained crude product
  9. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-b3200a419099463d8d92278568cfde65
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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