Dimethylacetamide → HCID 178462760, compound

HRID 579087Notes

Reaction equation

HRID 579087 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[C:21]([O:22]C)=[C:20]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([F:32])[C:25]=4[CH3:33])[CH:19]=[N:18]3)=[N:15][CH:16]=2)=[O:10])[CH2:5][CH2:4]1)[CH3:2].CC(N(C)C)=O.[Cl-].[Li+]>CS(C)=O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([N:17]3[C:21]([OH:22])=[C:20]([C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([F:32])[C:25]=4[CH3:33])[CH:19]=[N:18]3)=[N:15][CH:16]=2)=[O:10])[CH2:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 433294Lithium ChlorideHCID 1176004144-(1-(5-(4-ethylpiperazine-1-carbonyl)pyridin-2-yl)-5-methoxy-1H-pyrazol-4-yl)-2-fluoro-3-methylbenzonitrile

Product 1

HCID 178462760HCID 178462760, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combined 4-(1-(5-(4-ethylpiperazine-1-carbonyl)pyridin-2-yl)-5-methoxy-1H-pyrazol-4-yl)-2-fluoro-3-methylbenzonitrile (70 mg, 0.156 mmol) and DMA (1561 μl) then added lithium chloride (66.2 mg, 1.561 mmol) and heated at 70° C. overnight. The crude reaction was then diluted with DMSO (500 uL) and purified via preparative HPLC (acetonitrile-water, with TFA) to give the title compound (24.6 mg, 0.057 mmol, 36.3%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=7.33 Hz, 3 H) 2.33 (d, J=2.27 Hz, 3 H) 3.16 (t, J=7.20 Hz, 2 H) 3.24-4.06 (m, 8 H) 7.49-7.84 (m, 2 H) 8.04-8.30 (m, 2 H) 8.43 (br. s., 1 H) 8.60 (dd, J=2.15, 0.63 Hz, 1 H). ESI-MS m/z [M+H]+ 435.3.

Workup

  1. customThe crude reaction
  2. custompurified via preparative HPLC (acetonitrile-water, with TFA)

Sources & evidence

ORD record
ord-d715552415894ee2b6c6c42873da4617
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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