Acetyl chloride → HCID 46906794, compound

HRID 2074664Notes

Reaction equation

HRID 2074664 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-e509e37ce5d64009a57a3896e5d37212
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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