Hydrochloric Acid → HCID 67370777, compound

HRID 1890763Notes

Reaction equation

HRID 1890763 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[N:13][C:12]([N:15]3[CH2:20][CH2:19][CH:18]([N:21](C)[C:22](=O)OC(C)(C)C)[CH2:17][CH2:16]3)=[C:11]([CH3:30])[C:10]=2[CH3:31])=[CH:5][CH:4]=1)#[N:2].Cl>O1CCOCC1>[CH3:31][C:10]1[C:11]([CH3:30])=[C:12]([N:15]2[CH2:16][CH2:17][CH:18]([NH:21][CH3:22])[CH2:19][CH2:20]2)[N:13]=[N:14][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58486412tert-Butyl 1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl(methyl)carbamate

Product 1

HCID 67370777HCID 67370777, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Treat a solution of tert-butyl 1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl(methyl)carbamate (1.68 g, 3.99 mmol) in 1,4-dioxane (20 mL) with 4 M HCl in 1,4-dioxane (20 mL). Stir the resulting mixture at ambient temperature for 2 h. Concentrate the reaction mixture under reduced pressure. Dissolve the residue in MeOH, and pour onto an SCX column (Varian, 20 g). Rinse the column with MeOH and CH2Cl2, and elute the product with a 1:1 mixture of CH2Cl2 and 2 M NH3/MeOH. Concentrate under reduced pressure to afford the title compound as a yellow solid (1.28 g, quantitative). ES/MS m/z 322.2 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. dissolutionDissolve the residue in MeOH
  3. additionpour onto an SCX column (Varian, 20 g)
  4. washRinse the column with MeOH and CH2Cl2
  5. washelute the product
  6. additionwith a 1:1 mixture of CH2Cl2 and 2 M NH3/MeOH
  7. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-31e2bb2bf5fa40469978b1c6f83a497a
Source dataset
uspto-grants-2013_08
Patent number
US08507490B2

Reaction notes

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