Hydrochloric Acid → HCID 68594590, compound

HRID 220599Notes

Reaction equation

HRID 220599 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[H-].[Na+].Cl.Cl.[Cl:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([N:25]3[CH2:30][CH2:29][N:28]([CH2:31][C:32]4[CH:33]=[N:34][N:35]([CH3:38])[C:36]=4[CH3:37])[CH2:27][CH2:26]3)=[N:21][CH:22]=[CH:23][N:24]=2)=[CH:15][CH:14]=1.[I-].[Na+].Cl>CN(C)C=O.C(#N)C.O>[ClH:11].[CH3:38][N:35]1[C:36]([CH3:37])=[C:32]([CH2:31][N:28]2[CH2:27][CH2:26][N:25]([C:20]3[C:19]([C:16]4[CH:15]=[CH:14][C:13]([CH2:12][N:3]5[CH:4]=[CH:5][N:6]=[C:2]5[CH3:1])=[CH:18][CH:17]=4)=[N:24][CH:23]=[CH:22][N:21]=3)[CH2:30][CH2:29]2)[CH:33]=[N:34]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 685941603'-(4-chloromethyl-phenyl)-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

Product 1

HCID 68594590HCID 68594590, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Stir 2-methyl imidazole (164 mg, 2.00 mmol) in dry N,N-dimethylformamide (5 mL) under nitrogen. Add sodium hydride (60% weight dispersion in oil, 77 mg, 2.00 mmol), then stir for 1 hr. at room temperature. Add 3′-(4-chloromethyl-phenyl)-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (233 mg, 0.50 mmol) at room temperature, followed by sodium iodide (75 mg, 0.50 mmol). Stir at room temperature for 20 hr. Quench reaction with water (20 mL), extract with DCM (3×10 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate and purify by high pH reverse phase HPLC, and concentrate to give the free base. Dissolve the free base in acetonitrile and convert to the hydrochloride salt by adding 1 eq 2 M aq HCl solution. Add water and lyophilize to give the title compound as a light brown powder (124 mg, 52%). MS (ES): m/z=443 [M+H]+.

Workup

  1. customat room temperature
  2. customat room temperature
  3. customQuench
  4. customreaction with water (20 mL)
  5. extractionextract with DCM (3×10 mL)
  6. concentrationconcentrate
  7. custompurify by high pH reverse phase HPLC
  8. concentrationconcentrate
  9. customto give the free base

Sources & evidence

ORD record
ord-a99288f521174b8ca20852d22e969ce5
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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