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

HRID 242865ノート

反応式

HRID 242865 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-feb13c645ac34f978b06c17c791dad6f
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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