Triethylamine → HCID 59900489, compound

HRID 567837Notes

Reaction equation

HRID 567837 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([CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[CH2:31][NH2:32])[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:32][CH2:31][C@@H:27]2[CH2:28][CH2:29][CH2:30][N:26]2[CH2:25][CH:22]2[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 2285118266183-69-5

Product 2

HCID 222AmmoniaHCID 59900489HCID 59900489, compoundYield 175.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (400 mg, 1.22 mmol) and [(2S)-1-(cyclopropylmethyl)pyrrolidinyl]methylamine (WO 87,07271) (190 mg, 1.22 mmol) and triethylamine (0.51 ml, 3.67 mmol) in ethyl acetate (20 ml) was heated under reflux for 18 hrs. The cooled mixture was partitioned between water and ethyl acetate, the phases separated, and the organic layer dried over MgSO4 and concentrated under reduced pressure. The residual orange oil was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (96:3.5:0.5) as eluant to give the desired product as a yellow oil, (476 mg, 88%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hrs
  3. customThe cooled mixture was partitioned between water and ethyl acetate
  4. customthe phases separated
  5. dry with materialthe organic layer dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residual orange oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-df466d2dfbaf4642bc7986b7db150b59
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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