2-Amino-4-methylthiazole → HCID 10018986, compound

HRID 2213106Notes

Reaction equation

HRID 2213106 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=O.[NH2:19][C:20]1[S:21][CH:22]=[C:23]([CH3:25])[N:24]=1>C(O)C>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([C:3]2[N:19]=[C:20]3[N:24]([CH:2]=2)[C:23]([CH3:25])=[CH:22][S:21]3)[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 741432-Amino-4-methylthiazoleHCID 219565182-Bromo-1-[3-methoxy-4-(pyridin-2-yl)phenyl]ethan-1-one

Product 1

HCID 10018986HCID 10018986, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (300 mg, 0.98 mmol) and 2-amino-4-methylthiazole (112 mg, 0.98 mmol) in ethanol (5 mL) was heated to reflux for 2 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with a solution of saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL), then dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1) to afford 6-(3-methoxy-4-pyridin-2-ylphenyl)-3-methylimidazo[2,1-b][1,3]thiazole. 1H NMR (CD3OD, 500 MHz) δ 8.91 (d, 1H), 8.85 (s, 1H), 8.74 (t, 1H), 8.47 (d, 1H), 8.11 (t, 1H), 7.94 (d, 1H), 7.78 (s, 1H), 7.73 (d, 1H), 7.33 (s, 1H), 4.13 (s, 3H), 2.68 (s, 3H) ppm. MS (ESI) 322 (M)+.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with a solution of saturated aqueous sodium bicarbonate (10 mL) and brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1)

Sources & evidence

ORD record
ord-1ecefad0eb464311a94c62bb987e692a
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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