Pyridine → HCID 21083999, compound

HRID 347926Notes

Reaction equation

HRID 347926 reaction equation
[CH3:1][C:2]1[N:3]([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)[CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl.C1COCC1>[CH3:1][C:2]1[N:3]([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)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydride2×HCID 21084000HCID 21084000, compound

Product 1

HCID 21083999HCID 21083999, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the compound of Example 107 (93 mg, 0.20 mmol) and pyridine (32 μL, 0.4 mmol) in DCM (1 mL) was added trifluoroacetic anhydride (34 μL, 0.24 mmol) and the reaction stirred at r.t. for 30 mins. A further 60 μL of trifluoroacetic anhydride was added and the reaction stirred for 18 h before being diluted with DCM (10 mL) and THF (5 mL). The mixture was washed with 2M NaOH(aq), brine and the organic layer separated and dried over MgSO4. Solvent was removed in vacuo and the residue purified by column chromatography (silica, 2–5% MeOH in DCM) to give the title compound as a solid (60 mg, 67%). δH (CDCl3) 7.62 (1H, d, J 9.7 Hz), 7.51–7.44 (5H, m), 7.30–7.27 (2H, m), 7.01–6.98 (2H, m), 6.89 (2H, d, J 0.9 Hz), 6.61 (1H, d, J 9.7 Hz), 4.30–4.20 (4H, m), 2.43 (3H, s). LCMS (ES+) RT 2.46 minutes, 453 (M+H)+.

Workup

  1. stirringthe reaction stirred for 18 h
  2. washThe mixture was washed with 2M NaOH(aq), brine
  3. customthe organic layer separated
  4. dry with materialdried over MgSO4
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (silica, 2–5% MeOH in DCM)

Sources & evidence

ORD record
ord-9d01ce31908647a689386dc0baa44bd0
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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