Chlorosuccinimide → N-benzyl-5-chloro-4-(pyridin-2-yl)thiazol-2-amine

HRID 922872

Reaction equation

HRID 922872 reaction equation
[CH2:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20]N1C(=O)CCC1=O>CN(C=O)C>[CH2:1]([NH:8][C:9]1[S:10][C:11]([Cl:20])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2902584N-benzyl-4-(pyridin-2-yl)thiazol-2-amine

Product 1

HCID 58614641N-benzyl-5-chloro-4-(pyridin-2-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-benzyl-4-(pyridin-2-yl)thiazol-2-amine (60 mg, 0.23 mmol) in DMF (2 mL) was cooled to 0° C. and treated with N-chlorosuccinimide (33 mg, 0.25 mmol), and the reaction mixture was allowed to warm to room temperature. The solvent was evaporated, and the product was purified on reverse phase HPLC to produce N-benzyl-5-chloro-4-(pyridin-2-yl)thiazol-2-amine. MS (Q1) 302.2 (M)+.

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified on reverse phase HPLC

Sources & evidence

ORD record
ord-633c0b3efab743debbe6075fbd2ec801
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Linked notes

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