Sodium Iodide → HCID 53330902, compound

HRID 517977Notes

Reaction equation

HRID 517977 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:19]=[N:20][C:21]([O:28][CH2:29][CH2:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[N:14]=[C:13]([C:37]#[N:38])[C:12]=2[N:11]=[N:10]1.C(N(CC)C(C)C)(C)C.Cl[CH2:49][C:50]([CH3:53])([OH:52])[CH3:51].[I-].[Na+]>C(#N)C>[OH:52][C:50]([CH3:53])([CH3:51])[CH2:49][N:34]1[CH2:35][CH2:36][CH:31]([CH2:30][CH2:29][O:28][C:21]2[N:20]=[CH:19][C:18]([C:15]3[N:14]=[C:13]([C:37]#[N:38])[C:12]4[N:11]=[N:10][N:9]([CH3:8])[C:17]=4[CH:16]=3)=[CH:23][C:22]=2[C:24]([F:25])([F:26])[F:27])[CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 684091-Chloro-2-methylpropan-2-olHCID 81531DiisopropylethylamineHCID 866733511-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate

Product 1

HCID 53330902HCID 53330902, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 1-methyl-6-(6-(2-(piperidin-4-yl)ethoxy)-5-(trifluoromethyl)-pyridin-3-yl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile trifluoroacetate (70 mg) and N,N-diisopropylethylamine (85 mg) in acetonitrile (2 ml), 1-chloro-2-methylpropan-2-ol (48 mg) and sodium iodide (19 mg) were added and heated in microwave at 160° C. for 0.5 h. The reaction mixture was concentrated then diluted with dichloromethane and water, extracted with dichloromethane and separated by hydrophobic frits, concentrated. Purified by Strata Si column (5 g, dichloromethane:methanol=1:0, 25:1, 15:1, 12.5:1 to 10:1) then passed through Strata SCX column (1 g) to give 20.0 mg yellow amorphous as 6-(6-(2-(1-(2-hydroxy-2-methylpropyl)piperidin-4-yl)ethoxy)-5-(trifluoromethyl)pyridin-3-yl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (31%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthen diluted with dichloromethane and water
  3. extractionextracted with dichloromethane
  4. customseparated by hydrophobic frits
  5. concentrationconcentrated
  6. customPurified by Strata Si column (5 g, dichloromethane:methanol=1:0, 25:1, 15:1, 12.5:1 to 10:1)

Sources & evidence

ORD record
ord-07ba9c7621f94b33a1d285a4a5622305
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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