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

HRID 633022

Reaction equation

HRID 633022 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-6feebbc8861d4b5da3b074e8e21e8bf8
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Linked notes

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