Diisopropylethylamine → HCID 67340665, compound

HRID 1674763Notes

Reaction equation

HRID 1674763 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:25]1[CH:30]=[CH:29][C:28]2=[N:31][N:32]=[C:33]([C:34]([F:37])([F:36])[F:35])[N:27]2[N:26]=1>C(O)C>[F:36][C:34]([F:35])([F:37])[C:33]1[N:27]2[C:28]([CH:29]=[CH:30][C:25]([N:4]3[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]3)=[N:26]2)=[N:31][N:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 67340665HCID 67340665, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl 1,4-diazepane-1-carboxylate (4.00 g, 20.0 mmol) was added to a mixture of diisopropylethylamine (4.11 mL, 23.7 mmol) and 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (4.0 g, 18.2 mmol) in ethanol (80 mL). The mixture was heated under reflux for 6 hours and then allowed to cool to ambient temperature to give a precipitate. The precipitate was collected by filtration, washed with ethanol, and dried under vacuum to afford tert-butyl 4-[3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazin-6-yl]-1,4-diazepane-1-carboxylate (5.94 g, 85.4%) as a white solid. 1H NMR (300.132 MHz, DMSO) δ 1.15 (9H, d), 1.72-1.93 (2H, m), 3.27-3.39 (2H, m), 3.50-3.63 (2H, m), 3.66-3.75 (2H, m), 3.83 (2H, t), 7.46-7.56 (1H, m), 8.19-8.31 (1H, m); apparently as a mixture of rotamers; m/z 387 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customto give a precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f090ba03621d4653b3275a8cb84b06ba
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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