Triphenyl(3,3,3-trifluoropropyl)phosphanium iodide → 2-N-Methyl-2-N-phenyl-6-{5-[4-(3,3,3-trifluoropropylidene)piperidin-1-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamine

HRID 341441

Reaction equation

HRID 341441 reaction equation
[I-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])C=CC=CC=1.CC(C)([O-])C.[K+].[NH2:33][C:34]1[N:39]=[C:38]([N:40]([CH3:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:37]=[C:36]([C:48]2[N:52]=[C:51]([N:53]3[CH2:58][CH2:57][C:56](=O)[CH2:55][CH2:54]3)[O:50][N:49]=2)[N:35]=1>O1CCOCC1.C(Cl)Cl>[CH3:47][N:40]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]1[N:39]=[C:34]([NH2:33])[N:35]=[C:36]([C:48]2[N:52]=[C:51]([N:53]3[CH2:54][CH2:55][C:56](=[CH:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH2:57][CH2:58]3)[O:50][N:49]=2)[N:37]=1

Participants

6

Reactant 3

HCID 19694095Triphenyl(3,3,3-trifluoropropyl)phosphanium iodideHCID 23665647Potassium tert-butoxideHCID 668031631-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)piperidin-4-one2×

Product 1

HCID 668027052-N-Methyl-2-N-phenyl-6-{5-[4-(3,3,3-trifluoropropylidene)piperidin-1-yl]-1,2,4-oxadiazol-3-yl}-1,3,5-triazine-2,4-diamineYield 12%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of triphenyl-(3,3,3-trifluoro-propyl)-phosphonium iodide (146 mg, 0.30 mmol) in anhydrous dioxane (10 mL) at 0 C under nitrogen was added potassium tert-butoxide (34 mg, 0.3 mmol) portion-wise. The suspension was stirred for 10 min at 0 C and then added drop-wise to a solution of 1-{3-[4-amino-6-(methyl-phenyl-amino)-[1,3,5]triazin-2-yl]-[1,2,4]oxadiazol-5-yl}-piperidin-4-one (Intermediate 131, 55 mg, 0.150 mmol) in anhydrous dioxane (10 mL). The resulting reaction mixture was stirred at room temperature for 16 h and evaporated to dryness. The solid obtained was dissolved in DCM (25 mL) and washed with water (25 mL), a saturated ammonium chloride aq. solution (25 mL) and brine (25 mL). The organic phase was dried over magnesium sulfate, evaporated to dryness and purified by preparative HPLC-MS (Method B) to afford the title compound as an off-white solid (8 mg, 12%).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 16 h
  3. customevaporated to dryness
  4. customThe solid obtained
  5. washwashed with water (25 mL)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. customevaporated to dryness
  8. custompurified by preparative HPLC-MS (Method B)

Sources & evidence

ORD record
ord-5089c52427c043a3bfcd23c7bf57d7b5
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Linked notes

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