Sodium Carbonate → HCID 86677525, compound

HRID 1497862Notes

Reaction equation

HRID 1497862 reaction equation
[F:1][C:2]1([F:26])[CH2:5][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:25])=[C:15]([NH:17]C(=O)OC(C)(C)C)[CH:16]=3)[N:7]=2)[CH2:3]1.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C(F)(F)F)=O>[F:26][C:2]1([F:1])[CH2:3][CH:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:25])=[C:15]([CH:16]=3)[NH2:17])[N:7]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 71288110HCID 71288110, compound

Product 1

HCID 86677525HCID 86677525, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl (5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamate (36) (1.2 g, 3.3 mmol) was dissolved in TFA (10 mL) and stirred at room temperature for 15 minutes. Then TFA was removed under vacuum to give the residue which was neutralized by addition of 2M Na2CO3 solution (20 mL). The solution was extracted with EtOAc and the organic phase was dried over Na2SO4. Evaporation of solvent gave 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) as a white solid (0.9 g, 100% yield), which was used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 7.33 (d, J=1.2 Hz, 1H), 7.14 (dd, J=1.2, 7.6 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 5.37 (br, 2H), 3.84 (m, 1H), 2.98-3.24 (m, 4H), 2.12 (s, 3H). MS m/z 266.1 (M+1)+.

Workup

  1. customThen TFA was removed under vacuum
  2. customto give the residue which
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-53c1599a744d4f2dbf4a0af1507bc5a1
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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