Benzyl Bromide → HCID 66802462, compound

HRID 341423Notes

Reaction equation

HRID 341423 reaction equation
Cl.[CH3:2][N:3]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:4]1[N:9]=[C:8]([NH2:10])[N:7]=[C:6]([C:11]2[N:15]=[C:14]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[O:13][N:12]=2)[N:5]=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.C(Cl)Cl>[CH2:30]([N:19]1[CH2:18][CH2:17][CH:16]([C:14]2[O:13][N:12]=[C:11]([C:6]3[N:5]=[C:4]([N:3]([CH3:2])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:9]=[C:8]([NH2:10])[N:7]=3)[N:15]=2)[CH2:21][CH2:20]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 24758Sodium hydrideHCID 66802903HCID 66802903, compound2×

Product 1

HCID 66802462HCID 66802462, compoundYield 1.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-N-methyl-2-N-phenyl-6-[5-(piperidin-4-yl)-1,2,4-oxadiazol-3-yl]-1,3,5-triazine-2,4-diamine hydrochloride (Intermediate 105, 0.100 g, 0.257 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil, 0.012 g, 0.309 mmol) at 0 C and stirred for 5 min. Benzyl bromide (30.6 μL, 0.257 mmol) was added, the reaction mixture was warmed to room temperature and stirred for 18 h. The mixture was then heated at 45 C for 18 h and re-treated with benzyl bromide (30.6 L, 0.257 mmol). The mixture was then heated at 50 C for 18 h and stirred room temperature for 72 h. The reaction mixture was diluted with DCM and then washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified by preparative HPLC, Method A, to afford the title compound (2.2 mg, 1.9%).

Workup

  1. stirringstirred for 18 h
  2. temperatureThe mixture was then heated at 45 C for 18 h
  3. temperatureThe mixture was then heated at 50 C for 18 h
  4. stirringstirred room temperature for 72 h
  5. washwashed with a saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude compound was purified by preparative HPLC, Method A

Sources & evidence

ORD record
ord-0f399e37a7eb46d2b04a2ba8f7d47c7b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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