Stannous chloride dihydrate → HCID 86677530, compound

HRID 1497898Notes

Reaction equation

HRID 1497898 reaction equation
[CH3:1][O:2][C:3]1([C:22]([F:25])([F:24])[F:23])[CH2:6][CH:5]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=3)[N:8]=2)[CH2:4]1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1([C:22]([F:24])([F:25])[F:23])[CH2:4][CH:5]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH:13]=3)[NH2:19])[N:8]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 71281101HCID 71281101, compound

Product 1

HCID 86677530HCID 86677530, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A stirring mixture of 5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (124) (40 mg, 0.112 mmol) and tin (II) chloride dihydrate (101 mg, 0.448 mmol) in ethanol (2 mL) was heated at 65° C. for 2 hours. The reaction was cooled to room temperature and the pH was adjusted between 8-10 with saturated sodium bicarbonate. The slurry was filtered and washed with aqueous ethanol. The solvent was partially reduced and the crude product was extracted with ethyl acetate. The organic was washed with 1× water and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography to yield 5-(5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (125). 1H NMR (400 MHz, d6-DMSO) δ 10.24 (s, 1H), 10.13 (s, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.95 (dd, J=2.0, 9.6 Hz, 1H), 7.88-7.84 (m, 2H), 7.52 (d, J=8.4 Hz, 1H), 3.92-3.84 (m, 1H), 3.24-3.02 (m, 4H), 2.64 (s, 3H), 2.38 (s, 3H). MS m/z 433.16 (M+1)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe slurry was filtered
  3. washwashed with aqueous ethanol
  4. extractionthe crude product was extracted with ethyl acetate
  5. washThe organic was washed with 1× water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe crude product was purified by silica chromatography

Sources & evidence

ORD record
ord-1897088922d14e42805110585e3ff3d6
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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