Cesium carbonate → HCID 58327916, compound

HRID 659441Notes

Reaction equation

HRID 659441 reaction equation
[Cl:1][C:2]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)=[CH:14][C:6]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[CH3:33][N:34]([CH3:38])[CH2:35][CH2:36]Cl>CN(C=O)C>[Cl:1][C:2]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:15]3[CH:19]=[N:18][N:17]([CH2:36][CH2:35][N:34]([CH3:38])[CH3:33])[CH:16]=3)=[CH:14][C:6]1=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 57885831HCID 57885831, compound

Product 1

HCID 58327916HCID 58327916, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous DMF (2 mL) was added to a mixture of 1-(2-chloro-3,6-difluorobenzyl)-7-(1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-pyrido[2,3-b]pyrazine (57 mg, 0.000158 mol), cesium carbonate (0.110 g) and 2-dimethylaminoethyl chloride HCl (0.025 g). The reaction mixture was stirred at room temperature under nitrogen for 13 days and then concentrated and dissolved in methylene chloride. The organic phase was washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was purified on normal phase silica gel chromatography to give the title compound as an off-white solid (9% yield). LCMS: m/z=433.13 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.30 (6H, s), 2.79 (2H, t, J=6.8 Hz), 3.29 (2H, t, J=4.7 Hz), 3.51 (2H, m), 4.24 (2H, t, J=6.8 Hz), 4.50 (2H, s), 4.77 (1H, bs), 6.97 (1H, s), 7.02 (1H, m), 7.12 (1H, m), 7.60 (1H, s), 7.63 (1H, d, J=1.5 Hz), 7.66 (1H, s).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on normal phase silica gel chromatography

Sources & evidence

ORD record
ord-cc855dad45f24871b07007000859fed5
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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