Pyridine → HCID 67334934, compound

HRID 2102248Notes

Reaction equation

HRID 2102248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:11]([CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][N:17]([S:43]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)(=[O:45])=[O:44])[CH2:16][CH2:15]3)[N:11]([CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 68623162HCID 68623162, compound

Product 1

HCID 67334934HCID 67334934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the intermediate from Example 142 step F (156 mg, 0.35 mmol) in DCM (5 mL) was added pyridine (5 mL) and benzene sulfonyl chloride (68 μL, 0.53 mmol). After 4 hours the reaction was diluted with DCM and washed with 1N HCl (3×), dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography using 1:5 ethyl acetate-hexanes to give the title compound a white foam. 1H NMR (CDCl3, 500 MHz): δ 7.99(d, J=8.3 Hz, 2H), 7.8(d, J=8.7 Hz, 2H), 7.7(d, J=1.9 Hz, 2H), 7.67(t, J=7.3 Hz, 1H), 7.58(t, J=8.0 Hz, 2H), 7.32(t, J=1.8 Hz, 1H), 7.1(d, J=8.2 Hz, 2H), 6.42(s, 1H), 5.55(s, 2H), 3.93(s, 3H), 3.90(d, J=12.2 Hz, 2H), 2.46(m, 1H), 2.31(m, 2H), 1.77(m, 3H).

Workup

  1. washwashed with 1N HCl (3×)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e76d505aea8f4f3581c751baa9f78dc6
Source dataset
uspto-grants-2009_08
Patent number
US07572922B2

Reaction notes

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