Diisopropylethylamine → HCID 86639881, compound

HRID 2040807Notes

Reaction equation

HRID 2040807 reaction equation
O[C:2]1C(C)=CC(C(NO)=N)=C[C:3]=1OC.CC[N:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19].[CH2:24]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:57]([O:61][C:62](=[O:78])[CH2:63][CH2:64][C:65]1[C:70]([CH3:71])=[CH:69][C:68]([C:72](=[NH:75])[NH:73][OH:74])=[CH:67][C:66]=1[CH2:76][CH3:77])([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C.O.C([O-])(O)=O.[Na+].O1CCOCC1>[C:57]([O:61][C:62](=[O:78])[CH2:63][CH2:64][C:65]1[C:70]([CH3:71])=[CH:69][C:68]([C:72]2[N:75]=[C:2]([C:3]3[CH:20]=[C:18]([CH3:19])[N:17]=[C:21]([CH2:22][CH3:24])[CH:23]=3)[O:74][N:73]=2)=[CH:67][C:66]=1[CH2:76][CH3:77])([CH3:60])([CH3:59])[CH3:58]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178436624tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoateHCID 178492423HCID 178492423, compound

Product 1

HCID 86639881HCID 86639881, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of isonicotinic acid 4 (100 mg, 0.496 mmol) and DIPEA (193 mg, 1.49 mmol) in DMF (2 mL), PyBOP (273 mg, 0.525 mmol) is added at 0° C. The mixture is stirred at 0° C. for 15 min before 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid tert-butyl ester (152 mg, 0.496 mmol) is added. The mixture is stirred at rt for 1 h before it is diluted with water and aq. NaHCO3 solution. The mixture is extracted twice with ether. The combined org. extracts are dried over MgSO4, filtered and concentrated to give the crude hydroxyamidine ester intermediate (420 mg); LC-MS: tR=0.90 min, [M+1]+=454.47. This material is dissolved in dioxane and then stirred at 80° C. for 5 h. The solvent is evaporated to give crude 3-{2-ethyl-4-[5-(2-ethyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid tert. butyl ester; LC-MS: tR=1.07 min, [M+1]+=436.25.

Workup

  1. additionis added
  2. extractionThe mixture is extracted twice with ether
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude hydroxyamidine ester intermediate (420 mg)
  7. stirringstirred at 80° C. for 5 h
  8. customThe solvent is evaporated

Sources & evidence

ORD record
ord-9e41e8df5e26467e93a99878487e015a
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

Loading…