1,1,3,3-Tetramethylguanidine → HCID 68447717, compound

HRID 2233170Notes

Reaction equation

HRID 2233170 reaction equation
[F:1][C:2]1[C:3]([C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([O:12][CH3:13])=[N:5]2.[NH:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1.CN(C)C(N(C)C)=N>CN(C)C=O>[CH3:32][C:29]([O:28][C:27]([NH:26][CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH:14]([C:3]2[C:2]([F:1])=[CH:11][CH:10]=[C:9]3[C:4]=2[N:5]=[C:6]([O:12][CH3:13])[CH:7]=[N:8]3)[C:15]([O:17][CH3:18])=[O:16])[CH2:25][CH2:24]1)=[O:33])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 7238334-(N-Boc-amino)piperidineHCID 68447026HCID 68447026, compound

Product 1

HCID 68447717HCID 68447717, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 2-[6-fluoro-3-(methyloxy)-5-quinoxalinyl]-2-propenoate (13.64 g, 52.1 mmol), 1,1-dimethylethyl 4-piperidinylcarbamate (11.45 g, 57.3 mmol) and 1,1,3,3-tetramethylguanidine (3.12 ml) in dry dimethylformamide (300 ml) was heated at 65° C. (bath temp.) for 17 h. The solvent was evaporated and the residue was dissolved in ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate and the combined organic fractions were dried and evaporated. Chromatography on silica (1000 g), eluting with 2-5% methanol/dichloromethane gave the product (21.81 g, 91%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. customthe combined organic fractions were dried
  5. customevaporated
  6. washChromatography on silica (1000 g), eluting with 2-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-2e6ac7ae5702427a8192f42703b78e6f
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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