Triphenylphosphine → HCID 11530650, compound

HRID 2386927Notes

Reaction equation

HRID 2386927 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:20]1([CH2:26][CH2:27]O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:27][CH2:26][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 18232N-PiperidinoethanolHCID 779440HCID 779440, compoundHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 11530650HCID 11530650, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-methyl-3-(4-hydroxyphenyl)-4-(3H)quinazolinone synthesized according to Example 1-(1) and -(2) (100 mg, 0.40 mmol), 2-(1-piperidinyl)ethanol (89 mg, 0.50 mmol) and triphenylphosphine (125 mg, 0.50 mmol) were dissolved in dry tetrahydrofuran (2 mL) and cooled on an ice bath. Diethylazodicarboxylate (75 uL, 0.50 mmol) was dripped in at 0° C. and stirred at room temperature for 48 hours. The solvent was distilled off under reduced pressure, ether was added, the solid precipitate was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) and the title compound (124 mg, 86%) was obtained as a light brown oily substance.

Workup

  1. temperaturecooled on an ice bath
  2. customwas dripped in at 0° C.
  3. distillationThe solvent was distilled off under reduced pressure, ether
  4. additionwas added
  5. filtrationthe solid precipitate was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-462504a620744f438bc0e41dc8bea625
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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