Pyridine → HCID 25261082, compound

HRID 2246541Notes

Reaction equation

HRID 2246541 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-])=[O:4].[C:8]([O:11][C@@:12]1([CH2:44][CH3:45])[C:17]2[CH:18]=[C:19]3[N:27]([C:28](=[O:29])[C:16]=2[CH2:15][O:14][C:13]1=[O:43])[CH2:26][C:25]1[C:24]([CH2:30][CH2:31][Si:32]([CH3:38])([CH3:37])[CH2:33][CH2:34][CH2:35][NH3+:36])=[C:23]2[CH:39]=[CH:40][CH:41]=[CH:42][C:22]2=[N:21][C:20]3=1)(=[O:10])[CH3:9].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.N1C=CC=CC=1>ClCCl>[CH3:38][Si:32]([CH3:37])([CH2:33][CH2:34][CH2:35][NH:36][C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])[CH2:31][CH2:30][C:24]1[C:25]2[CH2:26][N:27]3[C:19](=[CH:18][C:17]4[C@@:12]([O:11][C:8](=[O:10])[CH3:9])([CH2:44][CH3:45])[C:13](=[O:43])[O:14][CH2:15][C:16]=4[C:28]3=[O:29])[C:20]=2[N:21]=[C:22]2[CH:42]=[CH:41][CH:40]=[CH:39][C:23]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 68530477HCID 68530477, compound

Product 1

HCID 25261082HCID 25261082, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Compound 21 (150 mg) in dichloromethane (2 mL) at 0° C., trifluoromethanesulfonic anhydride (80 μL) and pyridine were added and stirred at room temperature for 2 hours. Solvents were dried under vacuum and the crude residue was finally shaken between chloroform (2×10 mL) and 1 N HCl (5 mL). The collective organic layer was dried, evaporated and purified on a silica gel column using 2% ethanol in dichloromethane to obtain 96% of the required product (140 mg).

Workup

  1. customSolvents were dried under vacuum
  2. stirringthe crude residue was finally shaken between chloroform (2×10 mL) and 1 N HCl (5 mL)
  3. customThe collective organic layer was dried
  4. customevaporated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-25092dca94a54fe19b228e6ea22edcf1
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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