1,3,4-Thiadiazol-2-amine → HCID 21956514, compound

HRID 2213112Notes

Reaction equation

HRID 2213112 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]=[N: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)[N:23]=[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 199091,3,4-Thiadiazol-2-amineHCID 219565182-Bromo-1-[3-methoxy-4-(pyridin-2-yl)phenyl]ethan-1-one

Product 1

HCID 21956514HCID 21956514, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(3-methoxy-4-pyridin-2-ylphenyl)ethanone (150 mg, 0.49 mmol) and 2-amino-1,3,4-thiadiazole (49 mg, 0.49 mmol) in ethanol (3 mL) was heated to reflux for 2 h, then concentrated. The residue was dissolved in ethyl acetate (25 mL) and washed with saturated aqueous NaHCO3 (10 mL), brine (10 mL), 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)imidazo[2,1-b][1,3,4]thiadiazole. 1H NMR (CD3OD, 300 MHz) δ 9.28 (s, 1H), 8.91 (s, 1H), 8.84 (d, 1H), 8.68 (dt, 1H), 8.37 (d, 1H), 8.05 (ddd, 1H), 7.85 (d, 1H), 7.81 (br s, 1H), 7.72 (dd, 1H), 4.09 (s, 3H) ppm. MS (ESI) 309 (M)+.

Workup

  1. temperatureto reflux for 2 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. washwashed with saturated aqueous NaHCO3 (10 mL), 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-65fee3cbfd4a46e4bf4cf894cb557fa4
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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