2-Chloro-3-nitropyridine → N-((5-fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine

HRID 1848180Notes

Reaction equation

HRID 1848180 reaction equation
[F:1][C:2]1[C:3]([CH2:13][NH2:14])=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1.CCN(C(C)C)C(C)C.Cl[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=1>>[F:1][C:2]1[C:3]([CH2:13][NH:14][C:25]2[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:11])=[N:7][C:6]=2[CH:12]=1

Participants

4

Reactant 3

HCID 796132-Chloro-3-nitropyridineHCID 81531DiisopropylethylamineHCID 86681148(5-Fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanamine

Product 1

HCID 86681147N-((5-fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amineYield 84%

Procedure

To a stirred mixture of (5-fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methanamine (128 mg, 0.6 mmol) and DIEA (195 μL, 1.2 mmol) at 0° C. under argon was added 2-chloro-3-nitropyridine (98 mg, 0.7 mmol) in one portion. The mixture was stirred at rt for 18 h and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 50% EtOAc in hexanes to afford N-((5-fluoro-2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine (165 mg, 84%) as a yellow oil. LCMS (ESI) m/z 351 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel flash chromatography
  3. washeluting with a gradient of 100% hexanes to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-990e11bf521a4669bbb83ffbbdd198a9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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