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Sodium Iodide → HCID 59149823, compound

HRID 1675133
Notes
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Reaction equation

HRID 1675133 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[CH:27][C:28]4[N:29]([C:31]([C:34]([F:37])([F:36])[F:35])=[N:32][N:33]=4)[N:30]=3)[CH2:21][CH2:20]2)=[CH:15][CH:14]=1)=[O:11].[I-].[Na+]>C1COCC1.CC(N(C)C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:20][CH2:21][N:22]([C:25]4[CH:26]=[CH:27][C:28]5[N:29]([C:31]([C:34]([F:37])([F:35])[F:36])=[N:32][N:33]=5)[N:30]=4)[CH2:23][CH2:24]3)=[CH:15][CH:14]=2)=[O:11])[CH2:4][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 531671-MethylpiperazineHCID 673415912-chloro-N-[4-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]acetamide

Product 1

HCID 59149823HCID 59149823, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

1-Methylpiperazine (140 μl, 1.27 mmol) was added to 2-chloro-N-[4-[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]acetamide (139 mg, 0.317 mmol) and sodium iodide (10 mg, 0.063 mmol) in a mixture of THF (2 mL) and DMA (0.5 mL). The resulting solution was heated at 60° C. for 2 hours, then cooled and evaporated to give the crude product which was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% ammonia) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to give 2-(4-methylpiperazin-1-yl)-N-[4-[1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenyl]acetamide (111 mg, 70%) as a solid.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customto give the crude product which
  4. customwas purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  5. additionFractions containing the desired compound
  6. customwere evaporated to dryness

Sources & evidence

ORD record
ord-50381c96a1974adca5709a8421a9589a
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003649B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes