Sodium hydride → HCID 66803033, compound

HRID 341439Notes

Reaction equation

HRID 341439 reaction equation
[H-].[Na+].Cl.[NH:4]1[CH2:7][CH:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[N:18]=[C:17]([N:19]([CH3:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:15]([NH2:27])[N:14]=3)[N:9]=2)[CH2:5]1.[F:28][C:29]([F:40])([F:39])[CH2:30]OS(C(F)(F)F)(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:26][N:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:17]1[N:16]=[C:15]([NH2:27])[N:14]=[C:13]([C:10]2[N:9]=[C:8]([CH:6]3[CH2:5][N:4]([CH2:30][C:29]([F:40])([F:39])[F:28])[CH2:7]3)[O:12][N:11]=2)[N:18]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 66803026HCID 66803026, compound2×

Product 1

HCID 66803033HCID 66803033, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium hydride (60% dispersion in mineral oil, 16 mg, 0.41 mmol) in anhydrous DMF (20 mL) at 0 C was added 6-[5-(azetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-N-methyl-2-N-phenyl-1,3,5-triazine-2,4-diamine hydrochloride (Intermediate 129, 50 mg, 0.138 mmol) and trifluoromethanesulfonic acid 2,2,2-trifluoro-ethyl ester (160 mg, 0.69 mmol) under nitrogen. The reaction mixture was stirred at room temperature for 16 h and then was quenched with saturated ammonium chloride aqueous solution (10 mL) and evaporated to dryness. The solid obtained was dissolved in EtOAc (20 mL), washed with water (2×25 mL), dried over magnesium sulfate and evaporated to dryness. The resulting crude product was purified by silica chromatography (2% MeOH in DCM) and then further by preparative HPLC-MS (Method B) to afford the title compound as white solid (5 mg, 9%).

Workup

  1. customwas quenched with saturated ammonium chloride aqueous solution (10 mL)
  2. customevaporated to dryness
  3. customThe solid obtained
  4. washwashed with water (2×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe resulting crude product was purified by silica chromatography (2% MeOH in DCM)

Sources & evidence

ORD record
ord-e1d6e0949925417380f1dc589fc18f8b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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