(S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate → (S)-1-(1-cyclopropyl-7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine

HRID 2036594ノート

反応式

HRID 2036594 の反応式
[CH:1]1([NH:4][C:5]2[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][C:13](=O)[C@@H:14]([NH:16]C(=O)OC(C)(C)C)[CH3:15])[CH2:3][CH2:2]1>CC(O)=O>[CH:1]1([N:4]2[C:5]3[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=3[N:12]=[C:13]2[C@@H:14]([NH2:16])[CH3:15])[CH2:3][CH2:2]1

参加物

3

反応物 1

HCID 58459185(S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 58459327(S)-1-(1-cyclopropyl-7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A stirred solution of (S)-tert-butyl 1-(2-(cyclopropylamino)-3-fluorophenylamino)-1-oxopropan-2-ylcarbamate (651.7 mg, 1.932 mmol) in AcOH (20 mL) was heated at 60° C. for 30 min, after being concentrated under reduced pressure, the residue was subjected to 4 M HCl in 1,4-Dioxane (20 mL). The resultant mixture was stirred at rt for 40 min. The mixture was concentrated under reduced pressure and dissolved in water (5 mL) and then basified with 1 N NaOH to pH 9.5. The mixture was concentrated under reduced pressure and triturated with MeOH-CDM (1:1). The crude product was purified by column chromatography on a silica gel column using DCM-MeOH—NH4OH (9:1:0.05) as eluent to give (S)-1-(1-cyclopropyl-7-fluoro-1H-benzo[d]imidazol-2-yl)ethanamine: LC-MS (ESI) m/z 220.0 [M+H]+.

後処理

  1. concentrationafter being concentrated under reduced pressure
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutiondissolved in water (5 mL)
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customtriturated with MeOH-CDM (1:1)
  6. customThe crude product was purified by column chromatography on a silica gel column

出典と根拠

ORDレコード
ord-9deb13ecd48c454e9083b43b29d9e5a3
出典データセット
uspto-grants-2013_11
特許番号
US08575183B2

反応ノート

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