Acetyl chloride → HCID 58853262, compound

HRID 659979Notes

Reaction equation

HRID 659979 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:12][C:13]2[CH:18]=[N:17][CH:16]=[C:15]([Cl:19])[N:14]=2)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl>[Cl:19][C:15]1[N:14]=[C:13]([NH:12][CH:8]([C:4]2[CH:3]=[C:2]([NH:1][C:27](=[O:29])[CH3:28])[CH:7]=[CH:6][CH:5]=2)[CH2:9][CH2:10][CH3:11])[CH:18]=[N:17][CH:16]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 58853217HCID 58853217, compound

Product 1

HCID 58853262HCID 58853262, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-[1-(3-aminophenyl)butyl]-6-chloropyrazin-2-amine (0.10 g, 0.36 mmol) and triethylamine (100 μl, 0.72 mmol) in dichloromethane (3 mL) cooled to 0° C. was added acetyl chloride (31 μL, 0.43 mmol). The resulting mixture was stirred at room temperature for 18 h. then diluted with dichloromethane (10 mL) and washed with H2O (10 mL) and brine (10 mL). The organic phase was collected, dried and concentrated and the residue purified by flash chromatography eluting with ethyl acetate-hexane (1:1) to give pure product (94 mg, 82%).

Workup

  1. washwashed with H2O (10 mL) and brine (10 mL)
  2. customThe organic phase was collected
  3. customdried
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-51b0e436b35348a3967924822fcf513e
Source dataset
uspto-grants-2011_12
Patent number
US08084456B2

Reaction notes

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