Potassium Carbonate → 4-(6-Methyl-pyridin-2-yl)-5-quinolin-6-yl-thiazol-2-ylamine

HRID 917677Notes

Reaction equation

HRID 917677 reaction equation
Br.Br[CH:3]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=O.[NH2:23][C:24]([NH2:26])=[S:25].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:12][C:8]1[N:7]=[C:6]([C:4]2[N:23]=[C:24]([NH2:26])[S:25][C:3]=2[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 865927622-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide

Product 1

HCID 859564494-(6-Methyl-pyridin-2-yl)-5-quinolin-6-yl-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide (24.5 mg, 0.072 mmol), thiourea (7.5 mg, 0.094 mmol, 1.3 equiv), and potassium carbonate (0.11 mmol, 1.5 equiv) in ethanol (1 mL) is heated to 80° C. overnight. The resulting reaction mixture is cooled to ambient temperature and concentrated in vacuo. Reverse phase high pressure liquid chromatography (a gradient from 5-30% acetonitrile in 0.1% aqueous formic acid) provides 4-(6-Methyl-pyridin-2-yl)-5-quinolin-6-yl-thiazol-2-ylamine.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e158bba659ec4b8784891fd6c32ab2d8
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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