4,5-Dihydro-2-thiazolamine → HCID 9995482, compound

HRID 2213105Notes

Reaction equation

HRID 2213105 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][CH2:22][CH2:23][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)[CH2:23][CH2:22][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 156894,5-Dihydro-2-thiazolamineHCID 219565182-Bromo-1-[3-methoxy-4-(pyridin-2-yl)phenyl]ethan-1-one

Product 1

HCID 9995482HCID 9995482, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (200 mg, 0.65 mmol) and 2-amino-2-thiazoline (67 mg, 0.65 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)-2,3-dihydroimidazo[2,1-b][1,3]thiazole. 1H NMR (CD3OD, 300 MHz) δ 8.86 (d, 1H), 8.67 (t, 1H), 8.35 (d, 1H), 8.17 (s, 1H), 8.04 (m, 1H), 7.84 (m, 1H), 7.62 (s, 1H), 7.54 (m, 1H), 4.60 (m, 2H), 4.26 (m, 2H), 4.07 (s, 3H) ppm. MS (ESI) 310 (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-36282630e8eb4be3b1e7e325c5363b13
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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