Pyridine → HCID 11999037, compound

HRID 1364108Notes

Reaction equation

HRID 1364108 reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]2[S:10][C:11]3[C:17](=[O:18])[CH2:16][C:15]([CH3:20])([CH3:19])[CH2:14][C:12]=3[N:13]=2)[CH2:4]1.N1C=CC=CC=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:19][C:15]1([CH3:20])[CH2:14][C:12]2[N:13]=[C:9]([N:5]3[CH2:6][CH2:7][O:8][CH:3]([CH2:2][NH:1][S:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)(=[O:35])=[O:34])[CH2:4]3)[S:10][C:11]=2[C:17](=[O:18])[CH2:16]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 11999150HCID 11999150, compound

Product 1

HCID 11999037HCID 11999037, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 154 (0.10 g, 0.34 mmol) and pyridine (0.04 g, 0.51 mmol) in DCM (10 mL) was added benzenesulphonyl chloride (0.06 g, 0.34 mmol) and the reaction mixture was stirred at room temperature for 4 h. The solvent was then removed in vacuo and purification by preparative HPLC gave the title compound (0.03 g, 20%) as a white solid. δH (CDCl3) 7.90 (2H, dd, J 6.9 and 1.5 Hz), 7.60 (3H, m), 4.87 (1H, t, J 6.0 Hz), 4.00 (2H, m), 3.75 (1H, m), 3.60 (2H, m), 3.20 (2H, m), 3.00 (2H, m), 2.70 (2H, s), 2.40 (2H, s), 1.10 (6H, s). LCMS (ES+) 436.0 (M+H)+.

Workup

  1. customThe solvent was then removed in vacuo and purification by preparative HPLC

Sources & evidence

ORD record
ord-0432c24d0bbf41f1a339badf00c49f06
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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