Sodium Iodide → HCID 59149820, compound

HRID 1675131Notes

Reaction equation

HRID 1675131 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]4[N:31]([C:33]([C:36]([F:39])([F:38])[F:37])=[N:34][N:35]=4)[N:32]=3)[CH2:23][CH2:22]2)[CH:16]=1)=[O:13].[I-].[Na+]>C1COCC1.CC(N(C)C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][CH2:10][CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:28]=[CH:29][C:30]5[N:31]([C:33]([C:36]([F:39])([F:37])[F:38])=[N:34][N:35]=5)[N:32]=4)[CH2:23][CH2:22]3)[CH:16]=2)=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 67341116HCID 67341116, compound

Product 1

HCID 59149820HCID 59149820, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

1-Methylpiperazine (152 μl, 1.37 mmol) was added to 4-chloro-N-[3-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]butanamide (160 mg, 0.343 mmol) and sodium iodide (10 mg, 0.069 mmol) in a mixture of THF (2 mL) and DMA (0.5 mL). The resulting solution was heated at 60° C. for 16 hours, then cooled and evaporated to give the crude product, which was purified by flash chromatography on silica, eluting with a gradient of 0-10% 2M ammonia in methanol in DCM. The solvents were evaporated, then the resulting gum triturated with ether and the precipitate filtered and dried to give 4-(4-methylpiperazin-1-yl)-N-[3-[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]butanamide (87 mg, 48%) as a solid.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customto give the crude product, which
  4. customwas purified by flash chromatography on silica
  5. washeluting with a gradient of 0-10% 2M ammonia in methanol in DCM
  6. customThe solvents were evaporated
  7. customthe resulting gum triturated with ether
  8. filtrationthe precipitate filtered
  9. customdried

Sources & evidence

ORD record
ord-982621e2cb5e44aa9ac24f9dcfce91ca
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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