Ethanol → Methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

HRID 405789Notes

Reaction equation

HRID 405789 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][N:15]([C:17]([O-:19])=[O:18])[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[N+:20]([O-])=O.[CH3:23]CO>>[NH2:20][C:3]1[CH:4]=[C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][N:15]([C:17]([O:19][CH3:23])=[O:18])[CH2:14]3)[O:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 702EthanolHCID 712814803-(3-(4-Methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

Product 1

HCID 86677444Methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate

Conditions

Temperature
78 °C

Procedure

To a stirring suspension of methyl 3-(3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (30) (795 mg, 2.50 mmol) in EtOH (20 mL) was added stannous chloride dihydrate (2.3 g, 9.99 mmol). The reaction mixture was heated at 78° C. for 3 hours. Then, the reaction was cooled to room temperature and the solvent was partially concentrated. The pH was adjusted to slightly basic pH with a saturated solution of sodium bicarbonate. The resulting white suspension was filtered and washed with water and ethyl acetate. The aqueous was extracted with ethyl acetate and washed with water, brine and dried over anhydrous sodium sulfate. The solvent was concentrated to give methyl 3-(3-(3-amino-4-methylphenyl)-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate (31). 1H NMR (400 MHz, d6-DMSO) δ 7.32 (d, J=1.6 Hz, 1H), 7.12 (dd, J=1.6, 7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 5.19 (s, 2H), 4.38-4.31 (m, 2H), 4.27-4.20 (m, 1H), 4.19-4.16 (m, 2H), 3.60 (s, 3H), 2.10 (s, 3H). MS m/z 289.12 (M+1)+.

Workup

  1. temperatureThen, the reaction was cooled to room temperature
  2. concentrationthe solvent was partially concentrated
  3. filtrationThe resulting white suspension was filtered
  4. washwashed with water and ethyl acetate
  5. extractionThe aqueous was extracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-12ee0aab12ff49009d9ccc3b223b884e
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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