Sodium Iodide → HCID 59321766, compound

HRID 220604Notes

Reaction equation

HRID 220604 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[N:4]1.[I-].[Na+].Cl[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([N:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]4[C:32]([CH3:42])=[N:33][N:34]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH:35]=4)[CH2:26][CH2:25]3)=[N:20][CH:21]=[CH:22][N:23]=2)=[CH:14][CH:13]=1>CN(C=O)C>[CH3:42][C:32]1[C:31]([CH2:30][N:27]2[CH2:26][CH2:25][N:24]([C:19]3[C:18]([C:15]4[CH:16]=[CH:17][C:12]([CH2:11][N:4]5[N:5]=[CH:6][CH:7]=[N:3]5)=[CH:13][CH:14]=4)=[N:23][CH:22]=[CH:21][N:20]=3)[CH2:29][CH2:28]2)=[CH:35][N:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:33]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 68595408HCID 68595408, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 59321766HCID 59321766, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Add sodium hydride (173 mg, 4.33 mmol) to a solution of 1H-1,2,3-triazole (308 mg, 4.33 mmol) in DMF (3 mL). Maintain stirring under nitrogen for 1 hr then add sodium iodide (162 mg, 1.08 mmol) and a solution of 3′-(4-Chloromethyl-phenyl)-4-(3-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (495 mg, 1.08 mmol) in DMF (8 mL). Maintain stirring under nitrogen for 20 hr. Quench by adding water (10 mL), wash with DCM (3×10 mL) and discard the aq. phase. Concentrate to dryness to give a mixture of 4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3′-(4-[1,2,3]triazol-1-ylmethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl and 4-(3-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3′-(4-[1,2,3]triazol-2-ylmethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl. Purify first by preparative HPLC then by SCX-2® ion exchange chromatography, eluting with 2 M NH3 in MeOH. to give 4-(3-methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3′-(4-[1,2,3]triazol-2-ylmethyl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (98 mg). MS (ES): m/z=492 [M+H]+ 2 min.

Workup

  1. temperatureMaintain
  2. temperatureMaintain
  3. stirringstirring under nitrogen for 20 hr
  4. customQuench
  5. additionby adding water (10 mL)
  6. washwash with DCM (3×10 mL)
  7. concentrationConcentrate to dryness
  8. customto give
  9. customPurify first by preparative HPLC
  10. washby SCX-2® ion exchange chromatography, eluting with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-2ce3eb63dc5649499832eaac5db2f067
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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