Hydrochloric Acid → Vafidemstat

HRID 709417ノート

反応式

HRID 709417 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 66714983Vafidemstat収率 52%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f9e986d65594e9685d284f59c7860f7
出典データセット
uspto-grants-2015_11
特許番号
US09181198B2

反応ノート

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