2-Aminothiazole → HCID 11723599, compound

HRID 2213110Notes

Reaction equation

HRID 2213110 reaction equation
Br[CH:2]([CH3:19])[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.[NH2:20][C:21]1[S:22][CH:23]=[CH:24][N:25]=1>C(O)C>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([C:3]2[N:20]=[C:21]3[N:25]([C:2]=2[CH3:19])[CH:24]=[CH:23][S:22]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 21552-AminothiazoleHCID 219565192-Bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one

Product 1

HCID 11723599HCID 11723599, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-one (153 mg, 0.50 mmol) and 2-aminothiazole (50 mg, 0.50 mmol) in ethanol (1 mL) was heated to reflux for 12 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried (MgSO4), concentrated and purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1 to 1:0) to afford 6-(3-methoxy-4-pyridin-2-ylphenyl)-5-methylimidazo[2,1-b][1,3]thiazole. 1H NMR (CDCl3, 500 MHz) δ 8.73 (m, 1H), 7.94 (d, 1H), 7.88 (d, 1H), 7.73 (dt, 1H), 7.52 (s, 1H), 7.35 (dd, 1H), 7.34 (dd, 1H), 7.22 (m, 1H), 6.86 (dd, 1H), 3.98 (s, 3H), 2.66 (s, 3H) ppm. MS (ESI) 322 (M)+.

Workup

  1. temperatureto reflux for 12 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel eluting with EtOAc:hexanes (2:1 to 1:0)

Sources & evidence

ORD record
ord-fbe28aef313741ad8dca150a599a7cc7
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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