Pyridine → HCID 21084003, compound

HRID 347924Notes

Reaction equation

HRID 347924 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[C:24]([C:26]([NH2:28])=O)[S:25][C:17]3=4)=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:21](=[O:22])[CH:20]=[CH:19][C:18]4[C:23]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)=[C:24]([C:26]#[N:28])[S:25][C:17]3=4)=[CH:14][CH:15]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 21084004HCID 21084004, compound

Product 1

HCID 21084003HCID 21084003, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound of Example 104 (128 mg, 0.27 mmol) in dry DCM (1.5 mL) was added pyridine (44 μL, 0.54 mmol) followed by trifluoroacetic anhydride (46 μL, 0.32 mmol). TLC showed the reaction was complete after 5 minutes and the reaction was then diluted with DCM (20 mL) and washed with 2M NaOH(aq) (20 mL). The DCM layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was co-evaporated with toluene (2×15 mL) to give the title compound as a solid (73 mg). δH (CDCl3) 7.62 (1H, d, J 9.7 Hz), 7.51–7.45 (5H, m), 7.29–7.26 (2H, m), 7.08–7.04 (2H, m), 6.62 (1H, d, J 9.7 Hz), 4.14 (2H, t, J 5.6 Hz), 3.71–3.68 (4H, m), 2.81 (2H, t, J 5.6 Hz), 2.58–2.54 (4H, m). LCMS (ES+) RT 2.47 minutes, 458 (M+H)+.

Workup

  1. washwashed with 2M NaOH(aq) (20 mL)
  2. customThe DCM layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66a30b2ff2164d6e89317e73115d4751
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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