1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67170729, compound

HRID 552135Notes

Reaction equation

HRID 552135 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[CH:16]12[CH:21]([N:22]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]1[CH2:19][NH:18][CH2:17]2.N12CCCN=C1CCCCC2>O1CCOCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:18]3[CH2:19][CH:20]4[CH:16]([CH:21]4[NH2:22])[CH2:17]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12]([N:18]3[CH2:17][CH:16]4[CH:20]([CH:21]4[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:19]3)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18362029HCID 18362029, compoundHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 2

HCID 67170729HCID 67170729, compoundHCID 67172284HCID 67172284, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.225 g, 1.00 mmol) in 1,4-dioxane (10 mL) was added (3-aza-bicyclo[3.1.0]hex-6-yl)dibenzyl-amine (0.440 g, 1.200 mmol), 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.5 mL, 3.00 mmol) and tetrabutyl ammonium bromide (0.032 g, 0.10 mmol). The resulting mixture was stirred at reflux for 18 hours. 1,4-Dioxane was removed in vacuo and the obtained crude product was purified by column chromatography to yield the desired product, 6-(6-dibenzylamino-3-azabicyclo[3.1.0]hex-3-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide in 89% yield (0.415 g). 1H NMR (300 MHz, CDCl3) δ 8.00-7.96 (m, 1H), 7.94 (d, J=9.6 Hz, 1H), 7.33-7.21 (m, 10H), 6.56 (d, J=8.5 Hz, 1H), 3.65 (s, 5H), 3.55-3.48 (dd, J=7.0 and 6.3 Hz, 3H), 3.44 (s, 2H), 1.57-1.48 (m, 5H), 0.76-0.67 (m, 1H), 0.46-0.40 (m, 2H), 0.09-0.04 (m, 2H). MS (ES+) m/z 468 (M+1).

Workup

  1. temperatureat reflux for 18 hours
  2. custom1,4-Dioxane was removed in vacuo
  3. customthe obtained crude product
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0c7a1ba5cdd4400fad9124f49ed00dc2
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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