Dimethylamine → HCID 10388364, compound

HRID 720442Notes

Reaction equation

HRID 720442 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][CH3:31]>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]([N:30]([CH3:31])[CH3:29])=[NH:23])[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

4

Reactant 2

HCID 674DimethylamineHCID 10023400HCID 10023400, compound

Product 1

HCID 10388364HCID 10388364, compoundYield 90%

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 (0.050 g, 0.127 mmol) was dissolved in 1:1 MeOH/CHCl3 (15 mL). Hydrogen chloride gas was bubbled through the solution for 15 min. The reaction was tightly capped and sealed, stirred overnight at rt, and concentrated to dryness. The crude intermediate was dissolved in methanol (15 mL), and 2M dimethylamine (0.45 mL, 0.892 mmol) was added. The reaction was tightly capped and sealed and stirred overnight at rt, concentrated, and purified by reverse phase HPLC freeze-dried to afford the title compound (0.050 g, 89%): 1H NMR (CHCl3) δ9.30 (bs, 0.5H), 8.76 (bs, 0.5H), 7.42 (d, j=9.1 Hz, 2H), 6.96 (d, j=8.8 Hz, 2H), 3.84 (s, 3H), 3.68 (t, j=6.8 Hz, 2H), 3.51 (t, j=6.3 Hz, 2H), 3.14 (s, 3H), 3.10(s, 3H), 3.01 (t, j=6.8 Hz, 2H), 2.66–2.62 (m, 2H), 1.72–1.60(m, 4H) ppm; Mass Spec 438.3(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. concentrationconcentrated
  10. custompurified by reverse phase HPLC
  11. customfreeze-dried

Sources & evidence

ORD record
ord-3f17cc5d2f9a4ec99b779cf61f12e7d5
Source dataset
uspto-grants-2006_11
Patent number
US07135469B2

Reaction notes

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