Acetyl chloride → HCID 46906794, compound

HRID 1819098Notes

Reaction equation

HRID 1819098 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:31]([F:34])([F:33])[F:32])=[C:6]([CH:30]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[CH:19]=3)=[CH:17][C:9]1=2.[C:35](Cl)(=[O:37])[CH3:36].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:31]([F:32])([F:34])[F:33])=[C:6]([CH:30]=1)[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C:10]2[N:14]=[CH:15][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:25][CH2:26][N:27]([C:35](=[O:37])[CH3:36])[CH2:28][CH2:29]4)[CH:19]=3)=[CH:17][C:9]1=2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 46871653HCID 46871653, compound

Product 1

HCID 46906794HCID 46906794, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[5-chloro-2-(trifluoromethyl)benzyl]-7-(2-piperazin-1-yl-pyridin-4-yl)-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine (63 mg, 0.000129 mol) in anhydrous DMF (1 mL) was added acetyl chloride (0.012 mL) and triethylamine (0.020 mL). The mixture was stirred at room temperature under nitrogen overnight and then concentrated. The residue was purified on normal phase silica gel chromatography to give the title compound as a yellow solid (56% yield). m.p.=241° C., LCMS: m/z=531.31 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.15 (3H, s), 3.47 (2H, m), 3.52 (2H, m), 3.57 (2H, m), 3.62 (2H, m), 3.73 (4H, m), 4.61 (2H, s), 5.25 (1H, bs), 6.55 (2H, m), 6.69 (1H, d, J=5.3 Hz), 7.37 (1H, d, J=8.3 Hz), 7.52 (1H, s), 7.65 (1H, d, J=8.3 Hz), 7.78 (1H, bs), 8.12 (1H, d, J=5.3 Hz).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on normal phase silica gel chromatography

Sources & evidence

ORD record
ord-b7b4b252849f4663a93b02f668c73a67
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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