Diisopropylethylamine → HCID 67340980, compound
Reaction equation
CCN(C(C)C)C(C)C.Cl[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=2)[N:16]=1.[CH3:24][N:25]([CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CC(N(C)C)=O>[CH3:24][N:25]([CH:33]1[CH2:34][CH2:35][N:36]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=3)[N:16]=2)[CH2:37][CH2:38]1)[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:29])[CH3:30]Participants
Conditions
- Temperature
- 50 °C
Procedure
DIPEA (1.355 mL, 7.78 mmol) was added to 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.865 g, 3.89 mmol) and tert-butyl methyl(piperidin-4-yl)carbamate (1 g, 4.67 mmol) in DMA (15 mL). The resulting solution was stirred at 50° C. for 2 hours. The reaction mixture was evaporated and diluted with DCM (100 mL), and washed sequentially with water (100 mL) and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford tert-butyl methyl[1-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]carbamate (1.500 g, 96%) as a solid.
Workup
- customThe reaction mixture was evaporated
- additiondiluted with DCM (100 mL)
- washwashed sequentially with water (100 mL) and saturated brine (100 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- customto afford crude product
- customThe crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM
- customPure fractions were evaporated to dryness
Sources & evidence
- ORD record
- ord-f6ed4591333f42d6a3128a8d401fd4e3
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003649B2
Reaction notes
Loading…