Diisopropylethylamine → HCID 59149753, compound

HRID 1674976Notes

Reaction equation

HRID 1674976 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.[CH2:15]([N:22]1[CH2:27][C@@H:26]([CH3:28])[NH:25][CH2:24][C@@H:23]1[CH3:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:15]([N:22]1[C@@H:23]([CH3:29])[CH2:24][N:25]([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:26]([CH3:28])[CH2:27]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 23402345(2S,5R)-1-Benzyl-2,5-dimethylpiperazine

Product 1

HCID 59149753HCID 59149753, compoundYield 79%

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), (2S,5R)-1-benzyl-2,5-dimethylpiperazine (4.90 g, 24.00 mmol) and DIPEA (5.14 mL, 30.00 mmol) in DMF (40 mL) was heated at 125° C. for 2 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 75% EtOAc/isohexane. Pure fractions were evaporated to dryness to afford 6-[(2R,5S)-4-benzyl-2,5-dimethylpiperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (6.16 g, 79%) as a tan gum.

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 75% EtOAc/isohexane
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-d06c921039b64d7a9b9730f4b6ed5f94
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

Loading…