Sodium Iodide → HCID 59149823, compound

HRID 1675133Notes

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

Participants

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

temperaturecooled
customevaporated
customto give the crude product which
customwas purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
additionFractions containing the desired compound
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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