Phthalimide → HCID 59857670, compound

HRID 2378087Notes

Reaction equation

HRID 2378087 reaction equation
C1(=O)[NH:5]C(=O)C2=CC=CC=C12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O[CH:46]1[CH2:51][CH2:50][CH2:49][N:48]([C:52]2[N:56]([CH2:57][CH:58]=[C:59]([CH3:61])[CH3:60])[C:55]([C:62]([NH:64][CH2:65][C:66]3[C:75]4[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=4)[CH:69]=[CH:68][CH:67]=3)=[O:63])=[N:54][N:53]=2)[CH2:47]1>O1CCCC1>[NH2:5][CH:46]1[CH2:51][CH2:50][CH2:49][N:48]([C:52]2[N:56]([CH2:57][CH:58]=[C:59]([CH3:61])[CH3:60])[C:55]([C:62]([NH:64][CH2:65][C:66]3[C:75]4[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=4)[CH:69]=[CH:68][CH:67]=3)=[O:63])=[N:54][N:53]=2)[CH2:47]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67268684HCID 67268684, compound

Product 1

HCID 59857670HCID 59857670, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14 mg phthalimide, 65 mg triphenylphosphine and finally 50 μl of diisopropyl azodicarboxylate are added to a solution of 39 mg 3-(3-hydroxy-piperidin-1-yl)-4-(3-methyl-but-2-enyl)-5-(naphth-1-ylmethylaminocarbonyl)-4H-[1,2,4]triazole in 1 ml dry tetrahydrofuran. The solution is stirred for 14 h at ambient temperature and then evaporated to dryness. The residue is taken up in 2 ml of toluene and combined with 50 μl ethanolamine. After 4 h stirring at 80° C. the mixture is cooled to ambient temperature and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol/ammonium hydroxide 95:5:1->80:20:1).

Workup

  1. customevaporated to dryness
  2. stirringAfter 4 h stirring at 80° C. the mixture
  3. temperatureis cooled to ambient temperature
  4. customthe solvent is removed
  5. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol/ammonium hydroxide 95:5:1->80:20:1)

Sources & evidence

ORD record
ord-3913c11b3dec47eeb8bf27d11f455a66
Source dataset
uspto-grants-2008_12
Patent number
US07470716B2

Reaction notes

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