Triethylamine → HCID 59900484, compound

HRID 2228799Notes

Reaction equation

HRID 2228799 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].[CH:22]1([N:27]2[CH2:31][CH2:30][CH2:29][C@@H:28]2[CH2:32][NH2:33])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(OCC)(=O)C>[NH3:4].[Cl:1][C:2]1[N:7]=[C:6]([NH:33][CH2:32][C@H:28]2[CH2:29][CH2:30][CH2:31][N:27]2[CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]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

6

Reactant 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 59900574HCID 59900574, compound

Product 2

HCID 222AmmoniaHCID 59900484HCID 59900484, compoundYield 159.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (404 mg, 1.23 mmol) was added to a solution of [(2R)-1-cyclopentylpyrrolidinyl]methylamine (preparation 143) (208 mg, 1.23 mmol) in ethyl acetate (10 ml), followed by triethylamine (190 ml, 1.36 mmol), and the reaction heated under reflux overnight under a nitrogen atmosphere. The cooled mixture was diluted with ethyl acetate, washed with water, brine, then dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography using a Biotage™ (KP-Sil™ 60 Å silica gel) cartridge and an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 95:5:0.5) to give the desired product as a cream solid, (450 mg, 80%).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux overnight under a nitrogen atmosphere
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-80e18f18195241898ecc10fd280cce14
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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