Dimethylamine → HCID 11395566, compound

HRID 1244539Notes

Reaction equation

HRID 1244539 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:26])[N:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([CH3:27])=[N:10]2)=[CH:5][CH:4]=1.[CH3:28][NH:29][CH3:30]>CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]3[C:14](=[O:26])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([C:22]([N:29]([CH3:30])[CH3:28])=[NH:23])=[CH:24][CH:25]=4)[CH2:16][CH2:17][C:12]=3[C:11]([CH3:27])=[N:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 21919832HCID 21919832, compound

Product 1

HCID 11395566HCID 11395566, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Part A. 4-[1-(4-Methoxy-phenyl)-3-methyl-7-oxo-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-benzonitrile (0.250 g, 0.98 mmol) was dissolved in 1:1 MeOH/CHCl3 (30 mL). Hydrogen chloride gas was bubbled through the solution for 15 min, and it was then tightly capped and sealed. The reaction was stirred overnight at rt and then concentrated to dryness. The crude intermediate was dissolved in methanol (30 mL) and 2M dimethylamine (5.23 mL, 10.5 mmol) was added. The reaction was tightly capped and sealed and stirred overnight at rt. The reaction was concentrated and purified by reverse phase HPLC and freeze-dried to yield 4-[1-(4-methoxy-phenyl)-3-methyl-7-oxo-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-N,N-dimethyl-benzamidine (0.255 g, 71%): 1H NMR (CHCl3) δ 9.66 (s, 0.5H), 8.73 (s, 0.5H), 7.51–7.38 (m, 6H), 6.91 (d, j=8.8 Hz, 2H), 4.13(t, j=6.6 Hz, 2H), 3.80 (s, 3H), 3.33 (s, 3H), 3.06 (s, 3H), 2.96 (t,j=6.4 Hz, 2H), 2.35 (s, 3H) ppm; Mass Spec 404.3 (M+H)+.

Workup

  1. customHydrogen chloride gas was bubbled through the solution for 15 min
  2. customit was then tightly capped
  3. customsealed
  4. concentrationconcentrated to dryness
  5. dissolutionThe crude intermediate was dissolved in methanol (30 mL)
  6. customThe reaction was tightly capped
  7. customsealed
  8. stirringstirred overnight at rt
  9. concentrationThe reaction was concentrated
  10. custompurified by reverse phase HPLC
  11. customfreeze-dried

Sources & evidence

ORD record
ord-72c055592ea64bfc9f91c75e7210e06f
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

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