4-Fluorobenzoyl chloride → HCID 86672830, compound

HRID 1423021Notes

Reaction equation

HRID 1423021 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([Cl:10])=[N:8][CH:7]=[CH:6][N:5]=1.[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>ClCCl>[Cl:10][C:9]1[C:4]([CH2:3][NH:2][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:12]([F:11])=[CH:13][CH:14]=2)=[N:5][CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 42614233(3-Chloropyrazin-2-yl)methanamine hydrochloride

Product 1

HCID 86672830HCID 86672830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (900 mg, 5 mmol) in dichloromethane (25 mL) is added 4-fluorobenzoyl chloride (730 μL, 6.1 mmol) followed by DIPEA (2.0 mL, 11 mmol). After 1 day, the mixture is concentrated and diluted with saturated aqueous ammonium chloride and extracted with EtOAc (3×40 mL). The combined organic layers are washed with brine (3×25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is passed through a pad of silica gel using dichloromethane-heptane (1:1) to load the sample and then eluting with dichloromethane to afford N-(3-chloro-pyrazin-2-ylmethyl)-4-fluoro-benzamide as an oil which partially solidified.

Workup

  1. concentrationthe mixture is concentrated
  2. additiondiluted with saturated aqueous ammonium chloride
  3. extractionextracted with EtOAc (3×40 mL)
  4. washThe combined organic layers are washed with brine (3×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-631c5e2d7e6f4804a28c4a2f0c6a2a90
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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