2-Chlorobenzothiazole → HCID 86694198, compound

HRID 707338Notes

Reaction equation

HRID 707338 reaction equation
Cl.[N+:2]([C:5]1[C:6]([NH:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].Cl[C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1>CN1CCCC1.O>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:6]2[C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 45786881HCID 45786881, compound2×

Product 1

HCID 86694198HCID 86694198, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-nitro-N-(piperidin-4-yl)pyridine-2-amine hydrochloride (intermediate 58, 500 mg, 2.24 mmol) and 2-chloro-benzo[d]thiazole (379 mg, 2.24 mmol) in N-methylpyrrolidine (5 mL) was heated at 180° C. in microwave for 2 hours. The mixture was diluted with water (60 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by silica chromatography gave N-(1-(benzo[d]thiazol-2-yl)piperidin-4-yl)-3-nitropyridin-2-amine (270 mg, 0.76 mmol, 33.8% yield).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification by silica chromatography

Sources & evidence

ORD record
ord-cbe232cae2944ae697f510cdc8a39174
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…