2,3-Dichloropyrazine → HCID 10134283, compound

HRID 1827148Notes

Reaction equation

HRID 1827148 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1>C(OCC)(=O)C>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:17]([N:14]2[CH2:15][CH2:16][CH:11]([CH2:10][NH:9][C:2]3[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=3)[CH2:12][CH2:13]2)=[O:18])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 785752,3-DichloropyrazineHCID 22135582HCID 22135582, compound2×

Product 1

HCID 10134283HCID 10134283, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To 2,3-dichloropyrazine (0.160 gm, 0.00107 mol) was added 4-fluorobenzyl 4-(aminomethyl)piperidine-1-carboxylate (INTERMEDIATE 2C) (0.86 gm, 0.00322 mol) and the resulting mixture heated under nitrogen at 110° C. for 30 min. The reaction was cooled, diluted with ethyl acetate (5 mL), and washed with 10% aqueous sodium/citric acid pH=5.2 (3×30 mL), and 10% aqueous sodium bicarbonate (30 mL). The ethyl acetate extract was dried over sodium sulfate, filtered through a pad of silica and concentrated to an oil. Crystallization from ether/hexane gave 4-[(3-chloro-pyrazin-2-ylamino)-methyl]-piperidine-1-carboxylic acid 4-fluoro-benzyl ester.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with 10% aqueous sodium/citric acid pH=5.2 (3×30 mL), and 10% aqueous sodium bicarbonate (30 mL)
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered through a pad of silica
  6. concentrationconcentrated to an oil
  7. customCrystallization from ether/hexane

Sources & evidence

ORD record
ord-e98228a0c13340f99342ed5fd9fe5ae0
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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