Triphenylphosphine → HCID 22254613, compound

HRID 1611680Notes

Reaction equation

HRID 1611680 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]2.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[NH2:54][C:55]1[CH:64]=[CH:63][C:62]2[C:57](=[C:58]([O:65][CH:66]([CH3:71])[CH2:67][CH2:68][CH2:69]O)[CH:59]=[CH:60][CH:61]=2)[N:56]=1>C1COCC1>[CH3:71][CH:66]([O:65][C:58]1[CH:59]=[CH:60][CH:61]=[C:62]2[C:57]=1[N:56]=[C:55]([NH2:54])[CH:64]=[CH:63]2)[CH2:67][CH2:68][CH2:69][O:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([CH3:31])[CH:27]=[CH:26]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 132242-Methyl-8-hydroxyquinolineHCID 5387121Dibenzyl azodicarboxylate2×HCID 22254631HCID 22254631, compound

Product 1

HCID 22254613HCID 22254613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 20 mL scintillation vial with a septum cap was charged with PS-PPh3 resin (Aldrich Chemical Co., Inc, 90 mg, 4.4 equiv), 8-hydroxyquinaldine (1.5 equiv) and DBAD (22 mg, 1.6 equiv) and purged by passing a stream of N2 for 45 seconds. Anhydr. THF (3 mL) was added and the contents of the vial were shaken for 5 min. Then, a solution of 4-((2-aminoquinolin-8-yl)oxy)pentan-1-ol (15.0 mg/mL; 1.0 mL, 0.061 mmol)) in anhydr. THF (1 mL) was added and the resulting suspension was agitated at room temperature for 6 h. Following this, DBAD (22 mg, 1.6 equiv) was added and the mixture was agitated at room temperature for additional 12 h. The suspension was filtered, and the resin washed with THF (3×3.0 mL). The filtrate and washings were combined and evaporated in vacuo. The residue was then treated with 6.0 mL of 4 M HCl in dioxane at room temperature for 6 h. The resulting solution was evaporated in vacuo. The residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH and purified by preparative reverse-phase HPLC. 1H NMR (500 MHz, CDCl3) δ ppm 8.61 (d, 1H), 7.89 (d, 1H), 7.66 (m, 2H), 7.52 (d, 1H), 7.29 (m, 3H), 7.15 (m, 2H), 4.74 (m, 1H), 4.31 (m, 2H), 3.09 (s, 3H), 2.36 (m, 2H), 2.05 (m, 2H), 1.44 (d, 3H); MS (DCI/NH3) m/z 388 [M+H]+.

Workup

  1. customA 20 mL scintillation vial with a septum cap
  2. custompurged
  3. customfor 45 seconds
  4. additionTHF (3 mL) was added
  5. stirringthe resulting suspension was agitated at room temperature for 6 h
  6. additionwas added
  7. stirringthe mixture was agitated at room temperature for additional 12 h
  8. filtrationThe suspension was filtered
  9. washthe resin washed with THF (3×3.0 mL)
  10. customevaporated in vacuo
  11. additionThe residue was then treated with 6.0 mL of 4 M HCl in dioxane at room temperature for 6 h
  12. customThe resulting solution was evaporated in vacuo
  13. dissolutionThe residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH
  14. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-f252d3aa80ab4ba58c39c68f457f3cae
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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