Acetyl chloride → N-[6-(8-acetyloctahydro-2H-pyrazino[1,2-a]pyrazin-2-yl)-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethylpropanamide

HRID 2074930Notes

Reaction equation

HRID 2074930 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:37][CH2:36][N:35]4[CH2:38][CH2:39][NH:40][CH2:41][CH:34]4[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[C:53](Cl)(=[O:55])[CH3:54]>ClCCl>[C:53]([N:40]1[CH2:39][CH2:38][N:35]2[CH2:36][CH2:37][N:32]([C:21]3[N:20]=[CH:19][C:18]([N:16]([CH3:17])[C:14](=[O:15])[C:13]([C:5]4[CH:4]=[C:3]([C:2]([F:44])([F:1])[F:45])[CH:8]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:6]=4)([CH3:43])[CH3:42])=[C:23]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=4[CH3:31])[CH:22]=3)[CH2:33][CH:34]2[CH2:41]1)(=[O:55])[CH3:54]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 592157712-[3,5-bis(trifluoromethyl)phenyl]-N-[4-(4-fluoro-2-methyl phenyl)-6-(octahydro-2H-pyrazino[1,2-a]pyrazin-2-yl)-3-pyridinyl]-N,2-dimethylpropanamide

Product 1

HCID 15983979N-[6-(8-acetyloctahydro-2H-pyrazino[1,2-a]pyrazin-2-yl)-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of crude 2-[3,5-bis(trifluoromethyl)phenyl]-N-[4-(4-fluoro-2-methyl phenyl)-6-(octahydro-2H-pyrazino[1,2-a]pyrazin-2-yl)-3-pyridinyl]-N,2-dimethylpropanamide (prepared with an analogous procedure to that described for D80, 89 mg, 0.14 mmol) in 5 mL of dichloromethane were added at 0° C. triethylamine (197 μL, 1.41 mmol) and acetyl chloride (75 μL, 1.0 mmol). The reaction was left at room temperature for 2 h. It was diluted with dichloromethane, extracted with sat NaHCO3 solution, the organics dried (Na2SO4), and the solvent was removed. The product was purified by flash chromatography (silica, cyclohexane:EtOAc 50:50 to EtOAc). Obtained 60 mg.

Workup

  1. extractionextracted with sat NaHCO3 solution
  2. dry with materialthe organics dried (Na2SO4)
  3. customthe solvent was removed
  4. customThe product was purified by flash chromatography (silica, cyclohexane:EtOAc 50:50 to EtOAc)
  5. customObtained 60 mg

Sources & evidence

ORD record
ord-4d2cb29a0ba645d498a2f47da765367a
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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