Hydrochloric Acid → HCID 178494302, compound

HRID 1487980Notes

Reaction equation

HRID 1487980 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]2[C:8]([CH:16]3[CH2:19][CH2:18][CH2:17]3)=[CH:9][C:10]([CH3:15])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][N:3]=1.[OH-].[K+].Cl.[CH3:23]O>>[CH:16]1([C:8]2[C:7]([C:5]3[NH:1][C:2]([O:6][CH3:23])=[N:3][N:4]=3)=[CH:14][C:11]([C:12]#[N:13])=[C:10]([CH3:15])[CH:9]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 682888425-(5-Amino-1,3,4-oxadiazol-2-yl)-4-cyclobutyl-2-methylbenzonitrile2×

Product 1

HCID 178494302HCID 178494302, compoundYield 34%

Conditions

Temperature
85 °C

Procedure

To a solution of 5-(5-amino-1,3,4-oxadiazol-2-yl)-4-cyclobutyl-2-methylbenzonitrile (compound 89.6, 0.5 g, 2.0 mmol) in MeOH (40 mL) was added KOH (1.11 g, 20.0 mmol). The mixture was heated at 85° C. overnight, then cooled to 0° C. and neutralized to pH 7 with aqueous 1 M HCl. The mixture was extracted with EtOAc (×2), and the combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc 1:1 to EtOAc) to yield 0.2 g (34%) of the title compound as a white solid. m/z (ES+) 269 (M+H)+. 1H NMR (400 MHz, Chloroform-d) δ 10.96 (br, 1H), 7.82 (s, 1H), 7.35 (s, 1H), 4.11 (s, 3H), 4.15-4.05 (m, 1H), 2.59 (s, 3H), 2.31-2.16 (m, 2H), 2.14-1.89 (m, 3H), 1.87-1.71 (m, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc (×2)
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexanes:EtOAc 1:1 to EtOAc)

Sources & evidence

ORD record
ord-43abbb97b9d74bbfaae81971662ccd9d
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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