N-Methylethylenediamine → HCID 10366454, compound

HRID 720444Notes

Reaction equation

HRID 720444 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:24])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])[CH2:16][CH2:17][C:12]=3[C:11]([C:25]([F:28])([F:27])[F:26])=[N:10]2)=[CH:5][CH:4]=1.[CH3:29][NH:30][CH2:31][CH2:32]N.C(N(CC)CC)C>CO.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:24])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]4[N:30]([CH3:29])[CH2:31][CH2:32][N:23]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:25]([F:26])([F:27])[F:28])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8014N-MethylethylenediamineHCID 8471TriethylamineHCID 10023400HCID 10023400, compound

Product 1

HCID 10366454HCID 10366454, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

5-[1-(4-Methoxy-phenyl)-7-oxo-3-trifluoromethyl-1,4,5,7-tetrahydro-pyrazolo[3,4-c]pyridin-6-yl]-pentanenitrile (0.200 g, 0.510 mmol) was dissolved in 1:1 MeOH/CHCl3 (25 mL). Hydrogen chloride gas was bubbled through the solution for 15 min. The reaction was tightly capped and sealed, stirred overnight at rt, and then concentrated to dryness. The crude intermediate was dissolved in methanol (15 mL). N-Methylethylenediamine (0.04 mL, 0.510 mmol) and triethylamine (0.36 mL, 2.55 mmol) were 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 the title compound (0.184 g, 80%): 1H NMR (CHCl3) δ 7.43 (d, j=9.1 Hz, 2H), 6.95 (d, j=9.1 Hz, 2H), 3.95–3.83 (m, 2H), 3.85 (s, 3H), 3.71 (t, j=6.8 Hz, 2H), 3.58–3.50(m, 4H), 3.03 (t, j=7.9 Hz, 2H), 3.00(s, 2H), 2.68 (s, 4H), 1.73 (bs, 4H) ppm; Mass Spec 450.0(M+H)+.

Workup

  1. customHydrogen chloride gas was bubbled through the solution for 15 min
  2. customThe reaction was tightly capped
  3. customsealed
  4. concentrationconcentrated to dryness
  5. dissolutionThe crude intermediate was dissolved in methanol (15 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-9fc7ca98a749430a894c14b35bf915dc
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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