Water → 6'-[Acetyl-(3-chloro-benzyl)-amino]-2,3,5,6-tetra-hydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

HRID 2182175Notes

Reaction equation

HRID 2182175 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([NH:20][C:21](=[O:23])[CH3:22])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=1.[H-].[Na+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([N:20]([C:21](=[O:23])[CH3:22])[CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 207821571,1-Dimethylethyl 4-[6-(acetylamino)-2-pyrazinyl]-1-piperazinecarboxylate

Product 1

HCID 697323276'-[Acetyl-(3-chloro-benzyl)-amino]-2,3,5,6-tetra-hydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6′-acetylamino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-5b (36.9 mg, 0.11 mmol) and 1-bromomethyl-3-chloro-benzene (15.8 μL, 0.12 mmol) in DMF (1.1 mL) at room temperature was added 60% NaH in mineral oil (5 mg, 0.13 mmol). After stirring at room temperature for 4 h, the reaction mixture was poured into H2O (10 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×10 mL), brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude material was purified by preparative TLC using 50% ethyl acetate/ether with 1% NH4OH to afford the title compound I-5c (27.1 mg).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with H2O (3×10 mL), brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material was purified by preparative TLC

Sources & evidence

ORD record
ord-24b913fa8a5a4f18b2478ddaf8249abd
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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