Benzyl Bromide → HCID 59716760, compound

HRID 2224293Notes

Reaction equation

HRID 2224293 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:31](=[O:32])[N:11]3[NH:12][CH:13]([CH3:30])[C:14]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[C:15]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)[C:10]3=[N:9]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C=O)C>[F:36][C:2]([F:35])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:31](=[O:32])[N:11]3[N:12]([CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:13]([CH3:30])[C:14]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[C:15]([C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)[C:10]3=[N:9]2)=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59716562HCID 59716562, compound

Product 1

HCID 59716760HCID 59716760, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-6-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (15 mg, 0.028 mmol) prepared as described in Example 469 in DMF (0.5 mL) at RT was added K2CO3 (11.6 mg, 0.084 mmol), followed by benzyl bromide (9.6 mg, 0.056 mmol). The reaction was heated at 80° C. for overnight. The reaction was filtered. The collected solution was concentrated under educed pressure. The crude product was purified using reverse phase HPLC to give the title compound, 2-(4-(Trifluoromethyl)benzyl)-5-benzyl-7,8-bis(4-chlorophenyl)-6-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, (2 mg, 11%) as a white solid. HPLC retention time: 4.44 min; MS [M+H]+: found 621. 1H NMR (CDCl3, 400 MHz) δ 7.60 (d, 2H), 7.45 (d, 2H), 7.33-7.29 (m, 5H), 7.23-7.13 (m, 4H), 7.05-7.00 (m, 2H), 6.87-6.81 (m, 2H), 5.04 (s, 2H), 4.26-4.15 (m, 2H), 3.98-3.93 (q, 1H), 1.30 (d, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationThe collected solution was concentrated under educed pressure
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-97b0ed8a417a4a7bae9c026ca4700306
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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