Diisopropylethylamine → HCID 67340727, compound

HRID 1674980Notes

Reaction equation

HRID 1674980 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.[CH3:15][C@@H:16]1[CH2:21][NH:20][C@@H:19]([CH3:22])[CH2:18][N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][C@@H:16]1[CH2:21][N:20]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=3)[N:7]=2)[C@@H:19]([CH3:22])[CH2:18][N:17]1[C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 24903576tert-butyl (2R,5S)-2,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 67340727HCID 67340727, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (4.45 g, 20 mmol), (2R,5S)-tert-butyl 2,5-dimethylpiperazine-1-carboxylate (5.14, 24 mmol) and DIPEA (5.14 mL, 30.00 mmol) in DMF (40.0 mL) was heated at 125° C. for 2.5 hours. The reaction mixture was evaporated to dryness, redissolved in DCM and washed sequentially with 1M aqueous K2CO3, water and saturated brine. The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by MPLC silica chromatography, eluting with EtOAc. Product fractions were evaporated and triturated with ether. The solid was collected by filtration, washed with ether and dried under vacuum to afford (2R,5S)-tert-butyl 2,5-dimethyl-4-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazine-1-carboxylate (6.09 g, 76%) as a white crystalline solid.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM
  3. washwashed sequentially with 1M aqueous K2CO3, water and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by MPLC silica chromatography
  8. washeluting with EtOAc
  9. customProduct fractions were evaporated
  10. customtriturated with ether
  11. filtrationThe solid was collected by filtration
  12. washwashed with ether
  13. customdried under vacuum

Sources & evidence

ORD record
ord-0dcef6418d434871b599b20246ccbc0f
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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