Pyridine → HCID 18768960, compound

HRID 480259Notes

Reaction equation

HRID 480259 reaction equation
[C:1]([C:3]1([NH:10][C:11](=[O:30])[CH:12]([CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:13][C:14]([N:16]([CH2:21][CH3:22])[CH2:17][CH2:18][O:19]C)=[O:15])[CH2:5][CH:4]1[CH2:6]N(C)C)#[N:2].N1C=CC=CC=1.[O:37](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>ClCCl>[C:1]([C:3]1([NH:10][C:11](=[O:30])[CH:12]([CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:13][C:14]([N:16]2[CH2:21][CH2:22][O:19][CH2:18][CH2:17]2)=[O:15])[CH2:5][CH:4]1[CH2:6][OH:37])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 70039038HCID 70039038, compound

Product 1

HCID 18768960HCID 18768960, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the intermediate alcohol from Example 22 (1.1 g, 2.7 mmol) and pyridine (0.44 mL, 5.2 mmol) in dichloromethane (15 mL) at 0° C. was added Tf2O (0.67 mL, 4 mmol) slowly. The mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was washed with brine, dried (sodium sulfate) and purified by chromatography on silica gel (dichloromethane/MeOH=20/1) to give the title compound (0.35 g, 34.6%).

Workup

  1. washThe reaction mixture was washed with brine
  2. dry with materialdried (sodium sulfate)
  3. custompurified by chromatography on silica gel (dichloromethane/MeOH=20/1)

Sources & evidence

ORD record
ord-bcd1cd2b2afc4be68b495c64a713edd0
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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