Hydrochloric Acid → Vafidemstat

HRID 709417노트

반응식

HRID 709417 반응식
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[CH2:18][C@H:17]2[NH:19][CH2:20][C:21]2[O:25][C:24]([NH:26]C(=O)OC(C)(C)C)=[N:23][N:22]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[CH2:18][C@H:17]2[NH:19][CH2:20][C:21]2[O:25][C:24]([NH2:26])=[N:23][N:22]=2)=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 86695277Tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate

생성물 1

HCID 66714983Vafidemstat수율 52%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

HCl in 1, 4 dioxane (1 mL) was added to a solution of tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate (100 mg) in 1, 4 dioxane (1 mL) at 0° C. and stirred for 18 h. After completion, the solvent was evaporated and residue was dissolved in water (10 mL), basified with Na2CO3 solution, extracted with EtOAc (3×5 mL) The combined extracts were washed with water (5 mL), brine (5 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography using MeOH: CHCl3 (5:95) as eluent to afford 5-(((trans)-2-(4-(benzyloxy)phenyl)cyclopropylamino)methyl)-1,3,4-oxadiazol-2-amine (40 mg, 52%) as a white solid.

후처리

  1. customAfter completion, the solvent was evaporated
  2. dissolutionresidue was dissolved in water (10 mL)
  3. extractionextracted with EtOAc (3×5 mL) The combined extracts
  4. washwere washed with water (5 mL), brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-0f9e986d65594e9685d284f59c7860f7
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181198B2

반응 노트

불러오는 중…