Triphenylphosphine → HCID 178511735, compound

HRID 353920Notes

Reaction equation

HRID 353920 reaction equation
[N:1]([C@@H:4]1[CH2:7][C@H:6]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:26])[CH2:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[N:10]=[CH:9]2)[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[NH2:1][C@@H:4]1[CH2:5][C@H:6]([N:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:26])[CH2:15][C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[N:10]=[CH:9]2)[CH2:7]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 178514623HCID 178514623, compound

Product 1

HCID 178511735HCID 178511735, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[1-(cis-3-azido-cyclobutyl )-1H-imidazol-4-yl]-2-naphthalen-1-yl-acetamide (Preparation 4, Step 4; 330 mg, 0.95 mmol) was treated with triphenylphosphine (301 mg, 1.15 mmol) in tetrahydrofuran (10 mL) and water (1 mL) at 23° C. The solution was stirred at room temperature for 18 h. The solvent was removed in vacuo and the resulting residue was purified by silica gel chromatography (20:1:0.5 chloroform-methanol-ammonium hydroxide) to afford 289 mg (95% yield) of N-[1-(cis-3-amino-cyclobutyl)-1H-imidazol-4-yl]-2-naphthalen-1-yl-acetamide; 1H NMR (400 MHz, CD3OD) δ8.05 (d, J=7.5 Hz, 1H), 7.87 (d, J=7.9 Hz, 1H), 7.79 (d, J=9.0 Hz, 1H), 7.45 (m, 5H), 7.35 (s, 1H), 4.26 (m, 1H), 4.16 (s, 2H), 3.29 (m, 2H), 3.16 (m, 1H), 2.75 (m, 2H), 2.1 (m, 2H); MS (AP/Cl): 321.3 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by silica gel chromatography (20:1:0.5 chloroform-methanol-ammonium hydroxide)

Sources & evidence

ORD record
ord-e6bdbdf3fc3845a7aceb5d3c69c55d72
Source dataset
uspto-grants-2004_06
Patent number
US06756385B2

Reaction notes

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