2-Aminothiazole → HCID 78929369, compound

HRID 1785312Notes

Reaction equation

HRID 1785312 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10]Br)([CH3:4])[CH3:3].[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 78929369HCID 78929369, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of (3-bromopropyl)-carbamic acid 1,1-dimethylethyl ester (1.2 g, 5.0 mmol) and 2-aminothiazole (1.0 g, 10 mmol, 2 equiv.) in DMF 20 (mL) was added Cs2CO3 (2.5 g, 7.7 mmol, 1.5 equiv.). The resulting mixture was heated at 85° C. under N2 overnight. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (3×200 mL), and brine (200 mL). The organic phase was dried over Na2SO4, then concentrated in vacuo to afford an oil. The crude product was purified by chromatography (SiO2) using hexane/ethyl acetate to afford the title compound as a light yellow solid (300 mg).

Workup

  1. washwashed with water (3×200 mL), and brine (200 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto afford an oil
  5. customThe crude product was purified by chromatography (SiO2)

Sources & evidence

ORD record
ord-e8116cce19894db296c8126ece6ea845
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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