Water → HCID 21081842, compound

HRID 346509Notes

Reaction equation

HRID 346509 reaction equation
[N:1]1([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17]P(=O)(OCC)OCC)=[N:15][N:16]=3)[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[Br:32][C:33]1[CH:40]=[CH:39][CH:38]=[CH:37][C:34]=1[CH:35]=O.O>C1COCC1>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14](/[CH:17]=[CH:35]/[C:34]4[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=4[Br:32])=[N:15][N:16]=3)[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 811292-BromobenzaldehydeHCID 23665647Potassium tert-butoxideHCID 86597761HCID 86597761, compound

Product 1

HCID 21081842HCID 21081842, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl [(6-azepan-1-yl-1,2,4-triazolo[4,3-b]pyridazin-3-yl)methyl]phosphonate (367 mg) in THF (10 ml), potassium tert-butoxide (127 mg) was added with cooling in an ice bath, and the mixture was stirred at room temperature for 40 minutes. The resultant red solution was combined with 2-bromobenzaldehyde (0.128 ml), and stirred at room temperature for further 1 hour. The reaction solution was combined with water, and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant white solids were recrystallized from methanol to obtain 6-azepan-1-yl-3-[(E)-2-(2-bromophenyl)vinyl]-1,2,4-triazolo[4,3-b]pyridazine (152 mg) as colorless crystals.

Workup

  1. temperaturewith cooling in an ice bath
  2. stirringstirred at room temperature for further 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant white solids were recrystallized from methanol

Sources & evidence

ORD record
ord-7de38185b83c4d93bd079106bb070ae6
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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