Pyridine → HCID 90022792, compound

HRID 531440Notes

Reaction equation

HRID 531440 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[C:6]([CH:8]=1)[NH2:7].[CH3:15][S:16](Cl)(=[O:18])=[O:17].N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[C:6]([NH:7][S:16]([CH3:15])(=[O:18])=[O:17])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 26190367HCID 26190367, compound

Product 1

HCID 90022792HCID 90022792, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 17, 5-bromo-2-(2-(dimethylamino)ethoxy)aniline (1.8 g, 6.94 mmol) was mesylated with methanesulfonyl chloride (875 mg, 7.63 mol), pyridine (822 mg, 10.4 mmol), DCM (20 mL) to afford 1.97 g (83.12% yield) of the titled compound. 1H NMR (CDCl3, 300 MHz): δ 7.71-7.0 (d, 1H), 7.2-7.16 (dd, 1H), 6.92-6.89 (d, 1H), 4.07-4.04 (t, 2H), 2.92 (s, 3H), 2.56-2.53 (t, 2H), 2.35 (s, 6H).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-54d03510d9ad4836a7c7cda6a2a2b57f
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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