Diisopropylethylamine → HCID 67340864, compound

HRID 1675072Notes

Reaction equation

HRID 1675072 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[CH2:18][CH:17]([CH2:19][OH:20])[CH2:16]1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:12][C:11]([F:14])([F:13])[C:8]1[N:6]2[N:7]=[C:2]([N:15]3[CH2:18][CH:17]([CH2:19][OH:20])[CH2:16]3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 13400658(Azetidin-3-yl)methanol

Product 1

HCID 67340864HCID 67340864, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (4.44 g, 20.0 mmol), azetidin-3-ylmethanol (2.25 g, 22.0 mmol) and DIPEA (5.21 mL, 30.0 mmol) in DMF (40 mL) was heated at 70° C. for 1 hour. The solution was evaporated and partitioned between water and 2M aqueous K2CO3. The organic phase was washed with water and brine and dried over MgSO4. The crude product was purified by MPLC silica chromatography, eluting with 5% MeOH in DCM. Pure fractions were evaporated to dryness and triturated with ether, giving [1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]azetidin-3-yl]methanol (1.65 g, 30%) as a cream crystalline solid.

Workup

  1. customThe solution was evaporated
  2. custompartitioned between water and 2M aqueous K2CO3
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified by MPLC silica chromatography
  6. washeluting with 5% MeOH in DCM
  7. customPure fractions were evaporated to dryness
  8. customtriturated with ether

Sources & evidence

ORD record
ord-4027b068cdad4f588708155f4d261222
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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