Diisopropylethylamine → HCID 86639881, 화합물

HRID 2040807노트

반응식

HRID 2040807 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

HCID 86639881HCID 86639881, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e41e8df5e26467e93a99878487e015a
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580824B2

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