Potassium Carbonate → 4-Benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-thiazol-2-ylamine

HRID 917672Notes

Reaction equation

HRID 917672 reaction equation
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=O)[CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[NH+:15]=3)Br)=[CH:10][C:5]=2[O:4][CH2:3]1.[NH2:22][C:23]([NH2:25])=[S:24].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:22]=[C:23]([NH2:25])[S:24][C:12]=3[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 865927612-(2-Benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide

Product 1

HCID 114383414-Benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-thiazol-2-ylamineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(2-benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide (30 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) was heated to 80° C. overnight. The resulting reaction mixture was 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) provided 4-Benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-thiazol-2-ylamine (15.6 mg, 70%).[MS: M+H=312.0].

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbcb53da36ab40328defe8bc334ef4a6
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

Loading…