Water → HCID 22105517, compound

HRID 1455964Notes

Reaction equation

HRID 1455964 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][NH:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](I)[CH3:31].O>CN(C=O)C.C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:14]([CH:15]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)[CH2:30][CH3:31])=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22105618HCID 22105618, compound

Product 1

HCID 22105517HCID 22105517, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

Ethyl 4-(2-benzyloxypyrazin-3-ylmethylamino)benzoate (455 mg) was dissolved in dry DMF (4 mL) and added to a suspension of sodium hydride (51 mg of a 60% dispersion in mineral oil) in DMF (4 mL) precooled to 0° C. under argon dropwise over fifteen minutes. After stirring for thirty minutes at 0° C. ethyl iodide (0.12 mL) was added and the mixture stirred for 36 hours. The solution was poured into water (50 mL) and the mixture made acidic with glacial acetic acid. The organic phase was then extracted with ethyl acetate (3×50 mL), washed with water (50 mL) and brine (50 mL) and dried (MgSO4). After removal of the solvent, the residue was purified by MPLC (eluting 20% ethyl acetate in hexane, silica) to give ethyl 4-(1-(2-benzyloxypyrazin-3-yl)prop-1-ylamino)benzoate as an oil which was used in the next step without further purification, (260 mg).

Workup

  1. waitprecooled to 0° C. under argon dropwise over fifteen minutes
  2. additionwas added
  3. extractionThe organic phase was then extracted with ethyl acetate (3×50 mL)
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customAfter removal of the solvent
  7. customthe residue was purified by MPLC (eluting 20% ethyl acetate in hexane, silica)

Sources & evidence

ORD record
ord-51fba939eb2f4b49b6e6fc47e7d7c498
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

Loading…