Pyridine → HCID 59049327, compound

HRID 1264482Notes

Reaction equation

HRID 1264482 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C@@H:13]2[CH2:16][CH2:15][N:14]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=O)[CH:2]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH:39]=[N+:40]=[N-:41]>ClCCCl.ClCCl.CO>[CH2:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][C@H:13]1[C:11]1[N:10]([CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:41]=[N:40][N:39]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 24530Hydrazoic acidHCID 24819Phosphorus pentachlorideHCID 59049299HCID 59049299, compound

Product 1

HCID 59049327HCID 59049327, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-N-[3-(3-Pyridyl)-1-propyl]-1-(benzyloxycarbonyl)azetidine-2-carboxamide from Reference Example 16 (295.7 mg, 0.837 mmol, 1.0 eq) in dry 1,2-dichloroethane (8.5 mL) was added pyridine (100 μL, 1.24 mmol, 1.5 eq) under argon. Phosphorus pentachloride (263 mg, 1.26 mmol, 1.5 eq) was added in one portion and the mixture was stirred at about room temperature for about 4 hours. A dry HN3 solution (prepared by mixing 6.5 g of NaN3 in 25 mL of water with 8.3 mL conc. HCl, extracting with 25 mL 1,2-dichloroethane, drying over magnesium sulfate and filtering) was added and the reaction mixture was stirred at about room temperature overnight. The organic phase was washed with concentrated NH4OH solution (2×5 mL), dried and the solvents removed under vacuum. Flash chromatography (5-10% methanol in dichloromethane) gave 125.3 mg (40% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.11-3.51 (series of m, 7H); 4.08-5.40 (series of m, 6H); 7.12-7.57 (m, 7H); 8.37-8.51 (m, 2H).

Workup

  1. stirringthe reaction mixture was stirred at about room temperature overnight
  2. washThe organic phase was washed with concentrated NH4OH solution (2×5 mL)
  3. customdried
  4. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-c10b7ff60cb34600b0c027c85d0fe8a7
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

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