Triethylamine → HCID 18470857, compound

HRID 2228745Notes

Reaction equation

HRID 2228745 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21].[NH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[C:28]([NH:30][CH2:31][CH2:32][O:33][CH3:34])=O.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][CH2:23][CH2:24][C:25]2[CH:37]=[CH:36][CH:35]=[C:27]([CH2:28][NH:30][CH2:31][CH2:32][O:33][CH3:34])[CH:26]=2)[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 18470864HCID 18470864, compound

Product 1

HCID 18470857HCID 18470857, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (400 mg, 1.22 mmol) [see preparation 17] was added to a solution of 3-(2-aminoethyl)N-(2-methoxyethyl)benzamide (260 mg, 1.25 mmol) (see preparation 41] and triethylamine (0.34 ml, 2.4 mmol) in ethyl acetate (5 ml). The reaction mixture was heated to reflux for 4 hrs, after which time the mixture was cooled to room temperature and stirred for a further 56 hrs, the mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was washed with water (2×20 ml), brine (20 ml) and dried over MgSO4 the solvent was evaporated under reduced pressure. The crude product was purified by trituration with diethyl ether to afford the title compound, 365 mg, (60%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hrs
  3. customthe mixture was partitioned between ethyl acetate (20 ml) and water (20 ml)
  4. washThe organic layer was washed with water (2×20 ml), brine (20 ml)
  5. dry with materialdried over MgSO4 the solvent
  6. customwas evaporated under reduced pressure
  7. customThe crude product was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-176f97e00ac0444a9c9cf9876738aec9
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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