Diisopropylethylamine → HCID 67339770, compound

HRID 1675112Notes

Reaction equation

HRID 1675112 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.[C@@H:15]12[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@@H:19]([CH2:20][CH2:21]1)[CH2:18][NH:17][CH2:16]2.CCN(C(C)C)C(C)C>C(O)C>[F:12][C:11]([F:14])([F:13])[C:8]1[N:6]2[N:7]=[C:2]([N:17]3[CH2:16][C@H:15]4[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:19]([CH2:20][CH2:21]4)[CH2:18]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 12046220(1R,5S)-tert-Butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 67339770HCID 67339770, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (312 mg, 1.40 mmol), (1R,5S)-tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (312 mg, 1.47 mmol) and DIPEA (0.36 ml, 2.10 mmol) in ethanol (7.00 ml) was heated at 70° C. for 18 hours. On cooling a white precipitate formed which was collected by filtration, washed with ethanol (10 mL) and dried under vacuum to afford (1R,5S)-tert-butyl 3-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (384 mg, 69%) as a white crystalline solid.

Workup

  1. temperatureOn cooling a white precipitate
  2. customformed which
  3. filtrationwas collected by filtration
  4. washwashed with ethanol (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f8e76e238f534b6c92492b4d297b43d6
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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