Diisopropylethylamine → HCID 25493920, compound

HRID 1675082Notes

Reaction equation

HRID 1675082 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH:18]2[CH2:19][CH2:20][N:15]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=4)[N:7]=3)[CH2:16][CH2:17]2)=[CH:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 7022353-(4-Piperidinyl)-1H-indole

Product 1

HCID 25493920HCID 25493920, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.223 g, 1.0 mmol), 3-(piperidin-4-yl)-1H-indole (0.240 g, 1.20 mmol) and DIPEA (0.257 mL, 1.50 mmol) in DMF (3 mL) was heated at 70° C. for 1 hour. The reaction mixture was run onto an SCX cartridge, which was washed with MeOH and eluted with 2M ammonia in methanol. The crude product was purified by MPLC silica chromatography, eluting with ethyl acetate. Pure fractions were evaporated to a gum which crystallised on trituration with ether to afford 6-[4-(1H-indol-3-yl)piperidin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (0.119 g, 31%) as a colourless crystalline solid.

Workup

  1. washwas washed with MeOH
  2. washeluted with 2M ammonia in methanol
  3. customThe crude product was purified by MPLC silica chromatography
  4. washeluting with ethyl acetate
  5. customPure fractions were evaporated to a gum which
  6. customcrystallised on trituration with ether

Sources & evidence

ORD record
ord-8d4c4f9cf3994ec1a43ae27c64c61a07
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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