Sodium Iodide → HCID 178523836, compound

HRID 841922Notes

Reaction equation

HRID 841922 reaction equation
Cl[CH2:2][C:3]1[N:7]=[CH:6][NH:5][N:4]=1.[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[NH3:4].[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[C:23]([NH:25][C@H:26]1[CH2:30][CH2:29][N:28]([CH2:2][C:3]2[N:7]=[CH:6][NH:5][N:4]=2)[CH2:27]1)=[O:24]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 57068119(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamideHCID 178478450HCID 178478450, compound

Product 2

HCID 222AmmoniaHCID 178523836HCID 178523836, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(Chloromethyl)-1H-1,2,4-triazole (70.8 mg) [see Bazhenov D. N. et al, Zh. Org. Khim, (1994), 30(5), 791-792 and references cited therein] was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)pyrrolidin-3-yl]-2-piperidinecarboxamide (91.8 mg) [see Example 4], potassium carbonate (91 mg) and sodium iodide (10 mg) in acetonitrile (10 ml) at 0° C. The reaction mixture was stirred at room temperature for 18 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane:methanol: 0.88 aqueous ammonia solution to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-1-(1H-1,2,4-triazol-3-ylmethyl)pyrrolidin-3-yl]-2-piperidinecarboxamide (12.6 mg) as a solid.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 93:7:1, by volume, dichloromethane

Sources & evidence

ORD record
ord-bb6396423c194f6badb2721c54c96431
Source dataset
uspto-grants-2002_04
Patent number
US06372736B1

Reaction notes

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