Triphenylphosphine → 3-Cyclopentyl-5-ethyl-2-(2-ethyl-2h-[1,2,4]triazol-3-ylmethoxy)-8-phenylimidazo[1,2-d][1,2,4]triazine

HRID 396153Notes

Reaction equation

HRID 396153 reaction equation
[CH:1]1([C:6]2[N:10]3[C:11]([CH2:21][CH3:22])=[N:12][N:13]=[C:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:9]3=[N:8][C:7]=2[OH:23])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([N:26]1[C:30]([CH2:31]O)=[N:29][CH:28]=[N:27]1)[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([C:6]2[N:10]3[C:11]([CH2:21][CH3:22])=[N:12][N:13]=[C:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:9]3=[N:8][C:7]=2[O:23][CH2:31][C:30]2[N:26]([CH2:24][CH3:25])[N:27]=[CH:28][N:29]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanolHCID 230031883-Cyclopentyl-5-ethyl-8-phenylimidazo[1,2-d][1,2,4]triazin-2-ol

Product 1

HCID 98882163-Cyclopentyl-5-ethyl-2-(2-ethyl-2h-[1,2,4]triazol-3-ylmethoxy)-8-phenylimidazo[1,2-d][1,2,4]triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 12 a) (150 mg, 0.48 mmol) and (2-ethyl-2H-[1,2,4]triazol-3-yl)methanol (93 mg, 0.73 mmol) in tetrahydrofuran (5 ml) at 0° C. was added triphenylphosphine (192 mg, 0.73 mmol) followed by diethyl azodicarboxylate (110 μl, 0.73 mmol) dropwise with stirring. After 2 hours the tetrahydrofuran was evaporated in vacuo and the residue dissolved in dichloromethane (50 ml) and washed with water (2×20 ml). The organic phase was separated, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by prep. TLC (SiO2; 30% ethyl acetate in isohexane), and the product recrystallised from ether/isohexane to afford 35 mg (17%) as a white solid. δH (400 MHz; CDCl3) 1.43 (3H, t, J 7.2), 1.57 (3H, t, J 7.2), 1.71 (2H, m), 1.84 (2H, m), 2.02 (4H, m), 3.37 (2H, q, J 7.3), 3.66 (1H, quin, J 8.7), 4.30 (2H, q, J 7.2), 5.66 (2H, s), 7.53 (3H, m), 7.92 (1H, s), 8.54 (2H, m); m/z (ES+) 418 (M++H, 100%).

Workup

  1. customAfter 2 hours the tetrahydrofuran was evaporated in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (50 ml)
  3. washwashed with water (2×20 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by prep
  9. customTLC (SiO2; 30% ethyl acetate in isohexane), and the product recrystallised from ether/isohexane
  10. customto afford 35 mg (17%) as a white solid

Sources & evidence

ORD record
ord-8f8ba350b98048ccb87c281d93a68cf3
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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