O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 1-Amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate

HRID 2209259Notes

Reaction equation

HRID 2209259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]([C:8]#[C:9][CH3:10])=[N:6][CH:7]=1.[C:20]1([CH3:33])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[S:28]([O:31][NH2:32])(=[O:30])=[O:29]>CC#N>[CH3:27][C:22]1[CH:23]=[C:24]([CH3:26])[CH:25]=[C:20]([CH3:33])[C:21]=1[S:28]([O-:31])(=[O:30])=[O:29].[NH2:32][N+:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([O:11][CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:17])[CH3:18])[C:5]=1[C:8]#[C:9][CH3:10]

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 1239823045-Chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridine

Product 1

HCID 1317359841-Amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridine 6.58 (969 mg, 3 mmol) in MeCN (10 mL) was cooled to 0° C. under argon. O-(mesitylsulfonyl)hydroxylamine (700 mg, 3 mmol, prepared using a procedure similar to that reported in Org. Proc. Res. Dev. 2009, 13, 263-267) was added, and mixture was warmed to rt. After 2 hours, reaction mixture was concentrated under reduced pressure to yield 1-amino-5-chloro-2-(prop-1-yn-1-yl)-3-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-1-ium 2,4,6-trimethylbenzenesulfonate which was used in the next step without further purification. LCMS [M+H]+: 314.91.

Workup

  1. addition2009, 13, 263-267) was added
  2. customreaction mixture
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-96b2941141284b1885d4a2e2f983fc4a
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…