Acetonitrile → HCID 59644550, compound

HRID 2251996Notes

Reaction equation

HRID 2251996 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[C:19]3[C:20](=[N:24][O:25][C:26]=3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:33])[CH:21]=[N:22][N:23]=2)[N:9]=[N:8]1.C(#N)C>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].O>[NH2:24][C:20]1[C:19]([C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])=[O:25])=[C:18]([C:10]2[N:9]=[N:8][N:7]([CH2:6][C:5]3[CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=[C:3]([C:2]([F:41])([F:1])[F:42])[CH:4]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:23]=[N:22][CH:21]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 86760598HCID 86760598, compound

Product 1

HCID 59644550HCID 59644550, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 962WaterSolvent

Procedure

Combine 4-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-3-(2-chloro-phenyl)-isoxazolo[3,4-d]pyridazine (79 mg, 0.1314 mmol), acetonitrile (2.5 mL), water (131 μL), and molybdenum hexacarbonyl (17.4 mg, 0.066 mmol), and heat to 73° C. After 4 hours, cool to RT. Pour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm). Concentrate the dark liquid to 1.5 mL and apply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a EtOAc/hexanes gradient to provide 70 mg of a pink solid. Exact Mass 602.1: mass spectrum (IS): m/z=603.0 (M+1), 601.0 (M−1). 1H NMR (250 MHz, CDCl3) 8.62 (s, 1H), 7.75 (s, 1H), 7.45-7.32 (m, 3H), 7.28-7.10 (m, 3H), 7.00-6.80 (m, 3H), 6.10 (s, 2H).

Workup

  1. additionPour the mixture through a plug of Celite® (1 cm) and silica gel (2 cm)
  2. concentrationConcentrate the dark liquid to 1.5 mL
  3. washapply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-f754aebed34f4709bf42b91b1c21a43b
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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