(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 2036594노트

반응식

HRID 2036594 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-9deb13ecd48c454e9083b43b29d9e5a3
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575183B2

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