Pyridine → HCID 178463219, compound

HRID 2053720Notes

Reaction equation

HRID 2053720 reaction equation
FC(F)(F)S(OC)(=O)=O.[F:10][C:11]1[CH:22]=[CH:21][C:14]([CH2:15]N(C)C(=S)C)=[CH:13][CH:12]=1.[NH2:23][C:24]1[CH:33]=[C:32]2[C:27]([CH2:28][CH2:29][CH:30]([OH:49])[CH:31]2[NH:34][C:35]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:39][CH:38]=2)=[O:36])=[CH:26][CH:25]=1.[N:50]1[CH:55]=CC=[CH:52][CH:51]=1>C(Cl)Cl>[F:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][CH2:55][NH:50][C:51](=[N:23][C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][C@@H:30]([OH:49])[C@@H:31]3[NH:34][C:35]([C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[CH:39][CH:38]=3)=[O:36])=[CH:26][CH:25]=2)[CH3:52])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9526Methyl triflateHCID 21074313HCID 21074313, compoundHCID 86595227HCID 86595227, compound

Product 1

HCID 178463219HCID 178463219, compoundYield 2.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl trifluoromethanesulfonate (0.150 g, 0.915 mmol) to a solution of N-4-fluorobenzyl-N-methylthioacetamide (0.145 g, 0.736 mmol) in 10 mL of CH2Cl2 at room temperature. Stir the mixture for 30 minutes and remove the solvent under reduced pressure. Then add biphenyl-4-carboxylic acid (7-amino-2-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-amide (0.22 g, 0.61 mmol) followed by 5 mL of pyridine. Stir the resulting mixture for 12 h. After evaporate pyridine, purify the residue by column chromatography (silica gel, 5% MeOH in CH2Cl2) to give 10 mg of the title compound in 2.6% yield as a light yellow solid: 1H NMR (CDCl3) δ 7.89 (2H, d, J=8.0 Hz), 8.66 (2H, d, J=8.4 Hz), 7.61 (2H, d, J=7.2 Hz), 7.47 (2H, t, J=7.6 Hz), 7.39 (1H, t, J=7.6 Hz), 7.21 (1H, dd, J=6.0, 8.8 Hz), 6.98-7.05 (3 B, m), 6.72 (1H, s), 6.62 (1H, dd, J=2.0, 8.4 Hz), 6.56 (1H, d, J=7.2 Hz), 5.22 (1H, t, J=7.6 Hz), 4.60 (2H, s), 3.98-4.04 (2H, m), 3.41 (11H, t, J=6.0 Hz), 2.96 (3H, s), 2.85 (2H, t, J=4.8 Hz), 2.15-2.21 (2H, m), 1.87-1.95 (1H, m), 1.92 (3H, s), 1.60-1.64 (1H, m); MS 522 (MH+).

Workup

  1. customremove the solvent under reduced pressure
  2. stirringStir the resulting mixture for 12 h
  3. customAfter evaporate pyridine
  4. custompurify the residue by column chromatography (silica gel, 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1e74886a06dc41cb80b3689a137e2bd5
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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