Triphenylphosphine → HCID 58362440, compound

HRID 2361500Notes

Reaction equation

HRID 2361500 reaction equation
[N:1]([C:4]1[N:12]2[C:8](=[N:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=32)[CH:7]=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:5]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[NH2:1][C:4]1[N:12]2[C:8](=[N:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=32)[CH:7]=[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 86656001HCID 86656001, compound

Product 1

HCID 58362440HCID 58362440, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 1-azido-3-(4-Methoxyphenyl)-pyrido[1,2-a]benzimidazole (12.0 mg, 0.038 mmol) in benzene (2 mL) was added triphenylphosphine (15.0 mg, 0.057 mmol). The mixture was stirred at room temperature for 3 hours and concentrated to a residue. Methanol (2 mL) was added to above residue followed by HCl (conc., 1 mL). Reaction mixture was heated at 60° C. for 2 hours and concentrated. The residue was purified by HPLC (acetonitrile/water) to give 4.6 mg (42%) of T662 as a light yellow solid. 1H NMR (CD3OD): δ 8.50 (1H, d, J=8.8 Hz), 7.80 (2H, m), 7.72 (2H, m), 7.54 (1H, m), 7.27 (1H, s), 7.10 (2H, m), 6.99 (1H, s); MS: 290 (M+H+).

Workup

  1. concentrationconcentrated to a residue
  2. additionMethanol (2 mL) was added to above residue
  3. customReaction mixture
  4. temperaturewas heated at 60° C. for 2 hours
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC (acetonitrile/water)
  7. customto give 4.6 mg (42%) of T662 as a light yellow solid

Sources & evidence

ORD record
ord-6a0808cd247e4dcb9b806f07b14e405a
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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