Pyridine → HCID 24956164, compound

HRID 417934Notes

Reaction equation

HRID 417934 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[N:6]([C:10]3[S:11][C:12]4[C:18](=[O:19])[CH2:17][C:16]([CH3:21])([CH3:20])[CH2:15][C:13]=4[N:14]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:21][C:16]1([CH3:20])[CH2:15][C:13]2[N:14]=[C:10]([N:6]3[C:5]4[CH:22]=[CH:23][C:2]([NH:1][S:30]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)(=[O:32])=[O:31])=[CH:3][C:4]=4[O:9][CH2:8][CH2:7]3)[S:11][C:12]=2[C:18](=[O:19])[CH2:17]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 24956162HCID 24956162, compound

Product 1

HCID 24956164HCID 24956164, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 13 (46 mg, 0.14 mmol), benzenesulfonyl chloride (0.023 mL, 0.182 mmol) and pyridine (0.022 mL, 0.28 mmol) in DCM (4 mL) was stirred at r.t. for 5 h. The reaction mixture was concentrated in vacuo. Purification by prep HPLC gave the title compound as an off-white solid (23 mg, 35%). δH (CDCl3) 1.14 (6H, s), 2.43 (2H, s), 2.74 (2H, s), 4.08-4.16 (2H, m), 4.26-4.33 (2H, m), 6.64 (1H, dd, J 8.9, 2.4 Hz), 6.80 (1H, d, J 2.4 Hz), 7.02 (1H, s), 7.42-7.61 (3H, m), 7.77-7.87 (3H, m). LCMS (ES+) 470.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification by prep HPLC

Sources & evidence

ORD record
ord-e4fbbb747c304c52a858cf01c3d3cab5
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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