Trifluoroacetic acid → (S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine

HRID 242865노트

반응식

HRID 242865 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:11][CH3:12])[N:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:27]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH2:13])[CH2:11][CH3:12])[N:7]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:6]=2[CH:27]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68158046(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate

생성물 1

HCID 68157917(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propylamine수율 25%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate (234 mg, 0.63 mmol) in DCM (3 mL) was added TFA (1.5 mL) and the mixture was stirred at RT for 2 h. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM (20 mL) and a saturated solution of NaHCO3. The two phase system was stirred for 10 min, then the organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording (S)-1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propan-1-amine as a colourless oil (42 mg, 25%). LCMS: RT 1.90 min [M−NH2] 253.0

후처리

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM (20 mL)
  3. stirringThe two phase system was stirred for 10 min
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

출처 및 근거

ORD 기록
ord-feb13c645ac34f978b06c17c791dad6f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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