Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → US10023592, Example 208

HRID 575685Notes

Reaction equation

HRID 575685 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH2:13][O:14]C2CCCCO2)(=[O:11])=[O:10])=[CH:5][C:4]=1[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)[CH:29]=2)[C:24](=[O:37])[N:23]([CH3:38])[CH:22]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:14][CH2:13][CH2:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:31]4[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=4)[CH:29]=3)[C:24](=[O:37])[N:23]([CH3:38])[CH:22]=2)[CH:5]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1180220574-[2-Methoxy-5-[2-(oxan-2-yloxy)ethylsulfonyl]phenyl]-2-methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one

Product 1

HCID 118022109US10023592, Example 208Yield 24.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound of step 6 (80 mg, 0.15 mmol) and pyridinium p-toluensulfonate (59 mg, 0.31 mmol) in DCM (2 mL) were stirred at room temperature for 5 h. After purification by prep-TLC (DCM: MeOH=10:1), the title compound (16.47 mg, 24.4%) was obtained as an off-white solid. 1H NMR: (CDCl3, 400 MHz) δ8.49 (d, J=8.4 Hz, 1H), 8.05 (dd, J1=8.8 Hz, J2=2.4 Hz, 1H), 7.88 (d, J=2.4 Hz, 1H), 7.68 (s, 1H), 7.59-7.62 (m, 2H), 7.20 (d, J=8.8 Hz, 1H), 7.12 (d, J=1.2 Hz, 1H), 7.07 (s, 1H), 4.03-4.11 (m, 2H), 3.94 (s, 3H), 3.86 (s, 3H), 3.66 (s, 3H), 4.16 (t, J=5.2 Hz, 2H), 2.72 (t, J=6.4 Hz, 1H). LCMS: 454.1 (M+H)+

Workup

  1. customAfter purification by prep-TLC (DCM: MeOH=10:1)

Sources & evidence

ORD record
ord-4048f61ccc7742a28227c3890302b7ef
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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