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

HRID 1364648

Reaction equation

HRID 1364648 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-8233f7d92a354f708951ac2c74f968d1
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Linked notes

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