Triphenylphosphine → HCID 22180039, compound

HRID 1795961Notes

Reaction equation

HRID 1795961 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=[C:9]1[CH:19]([CH:21]1[CH2:23][CH2:22]1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:24]=[N+]=[N-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[NH2:24][CH:19]([CH:21]1[CH2:23][CH2:22]1)[C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[C:17]([Cl:18])[N:11]2[N:10]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 22180051HCID 22180051, compound

Product 1

HCID 22180039HCID 22180039, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-benzyl-7-chloro-2-(cyclopropyl-hydroxy-methyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 17 G, 0.10 g, 0.29 mmol) and sodium azide (30 mg, 0.46 mmol) in DMF (2 mL) was stirred at rt under nitrogen overnight. The reaction mixture was diluted with EtOAc to 40 mL, washed with water and brine, dried over MgSO2 and concentrated to a pale oil. The oil was dissolved in THF (6 mL) and water (0.2 mL), flushed with nitrogen and treated with triphenylphosphine (0.15 g, 0.58 mmol). The reaction mixture was heated at 66° C. for 5 h. The solvents were removed under reduced pressure. Purification of the residue by flash column chromatography (SiO2, EtOAc/hexane/MeOH/NH4OH 500:500:50:5) gave the title compound as a colorless oil (69 mg, 73%): 1H NMR (CDCl3) δ 7.35 (m, 4H), 7.22 (d, 1H, J=7.7 Hz), 7.11 (m, 1H), 6.54 (m, 1H), 5.65 (m, 1H), 5.37 (m, 1H), 3.73 (m 1H), 2.00 (m, 1H),1.60 (m, 1H), 1.33 (m, 1H), 0.58 (m, 1H), 0.29 (m, 2H); MS (ESI+) 329.09, 331.07 (M++H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO2
  3. concentrationconcentrated to a pale oil
  4. dissolutionThe oil was dissolved in THF (6 mL)
  5. customwater (0.2 mL), flushed with nitrogen
  6. temperatureThe reaction mixture was heated at 66° C. for 5 h
  7. customThe solvents were removed under reduced pressure
  8. customPurification of the residue by flash column chromatography (SiO2, EtOAc/hexane/MeOH/NH4OH 500:500:50:5)

Sources & evidence

ORD record
ord-1fb34c871e8c45a79affe8cb297b0a52
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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