O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 1,2-Diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate

HRID 1802182Notes

Reaction equation

HRID 1802182 reaction equation
[C:1]1([CH3:14])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:12][NH2:13])(=[O:11])=[O:10].[NH2:15][C:16]1[CH:17]=[C:18]([C:23]([F:26])=[CH:24][N:25]=1)[C:19]([O:21][CH3:22])=[O:20]>ClCCl.C(OCC)C>[CH3:8][C:3]1[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:14])[C:2]=1[S:9]([O-:12])(=[O:11])=[O:10].[NH2:13][N+:25]1[CH:24]=[C:23]([F:26])[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[NH2:15]

Participants

5

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 67777217Methyl 2-amino-5-fluoroisonicotinate

Product 1

HCID 866660181,2-Diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonateYield 81.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled white suspension of O-(mesitylsulfonyl)hydroxylamine (1.18 g, 5.48 mmol) in dichloromethane (8.44 ml) is added dropwise a solution of methyl 2-amino-5-fluoroisonicotinate (932 mg, 5.48 mmol) in dichloromethane (2.53 ml). The resulting light brown suspension is stirred for 2 hours at room temperature. The suspension is cooled to −5-0° C., diluted with diethylether (15 ml) and stirred for 30 minutes. The solid is collected by filtration, washed with diethyl ether and dried affording 1,2-diamino-5-fluoro-4-(methoxycarbonyl)pyridinium 2,4,6-trimethylbenzenesulfonate (1.72 g, 81.4%) as a light brown solid. MS: m/z=186.0 (M+).

Workup

  1. temperatureThe suspension is cooled to −5-0° C.
  2. stirringstirred for 30 minutes
  3. filtrationThe solid is collected by filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-73fd0b8537fd408da9189c55c488073f
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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