Triphenylphosphine → HCID 86640600, compound

HRID 2047316Notes

Reaction equation

HRID 2047316 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:47]1[O:49][C@@H:48]1[CH2:50]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:26]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([O:22][CH2:50][C@@H:48]4[CH2:47][O:49]4)=[C:17]([CH2:23][CH3:24])[CH:16]=3)[N:11]=2)[CH:7]=[C:6]([CH3:25])[N:5]=1)[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5460455(+)-GlycidolHCID 5462977Diethyl azodicarboxylateHCID 1363758784-(5-(2-(Diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol

Product 1

HCID 86640600HCID 86640600, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (110 mg, 0.30 mmol) in THF (9 mL), PPh3 (150 mg, 0.57 mmol) and (R)-glycidol (42 mg, 0.57 mmol) are added. The mixture is cooled to 0° C. before DEAD (248 mg, 0.57 mmol) is added. The mixture stirred for 1 h and is warmed to rt. The solvent is evaporated and the crude product is purified by CC on silica gel eluting with heptane:EA 7:3 to give diethyl-{4-[3-((S)-3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridin-2-yl}-amine (119 mg) as a yellow oil; LC-MS: tR=0.95 min; [M+1]+=423.21.

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. customthe crude product is purified by CC on silica gel eluting with heptane:EA 7:3

Sources & evidence

ORD record
ord-69892942e7574e0da8a314d22dff35fc
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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